We’ve posted a huge collection of news stories regarding all of Apple’s iOS 5 and iCloud announcements today, and wanted to give you all an opportunity to discuss everything in one central location in advance of our editorial on the topic.
Did Apple impress you with the collection of features added to iOS 5? Are you excited or glad to hear about the free services coming in iCloud? Was anything really important missing today? Sound off in the comments section below.
88 comments
Also (#2)
What is this $25.00 fee for music purchased or uploaded elsewhere? Are you telling me that I have to pay again for music I’ve already paid for in order for Apple to let me listen to it? This seems absurd to me. Ugh.
For those that keep referencing “Streaming” for the iTunes/iCloud integration, you are mistaken. This is not a streaming service. This is an “availability” service. If you have purchased a track/album via iTunes, you can now access that track via iCloud to simply re-download that track on the go. So, if you purchased a song on your computer but did not sync it to your iPhone, you can simply connect and retrieve it on the go. No streaming. The track now physically resides on your device.
And the iTunes Matching sounds like it will work the same. Once your non-iTunes purchased tracks have been identified and matched (for those that can be) you will simply have that same identifier showing “ownership” and be allowed to physically download a copy to whatever device you need it on (within the compatible devices…and limited to 10 devices). So, my curiosity in this is simply “Can you pay the $25 fee, reacquire all your non-iTunes Store tracks as the 265Kbps AAC files and then un-enroll and keep those songs?”. That is the only real unknown for me right now.
So, I do not really see a down side here. There is now risk of losing tracks in the event of a server catastrophe, you no longer need to rely on back-ups of your music (as it is available for re-download) and your existing music collection can be upgraded and included in the service for a very nominal fee. Sign me up (after clarifying that little nugget about opting out yet keeping your converted music)!
@drakebullet – I honestly think you are looking at this all wrong. Apple is not charging you one penny to listen to music you already bought. Sync it and listen to it. Apple and the labels are charging a pretty nominal fee to make that music universally accessible. They are charging for the convenience of having “reach back” capability to reacquire that music at any time and from any compatible device.
I have roughly 800 CD’s that I ripped into MP3 or AAC format so that I could load them onto my first iPod. I have since stopped buying CD’s and moved on to digital downloads (iTunes, Amazon, etc.) because the few CD’s I did still buy got ripped and quickly stored away. Why eat up valuable real estate with items that I would rarely (if ever) touch again? Now this iTunes in iCloud is going to let me access EVERY track from almost ANYWHERE. This matching is simply a way for Apple to make these tracks available with the least amount of effort on both ends. They simply have to create aliases under your account that point to the already existing digital tracks on their servers. That saves them storage space and you bandwidth AND time needed to upload all your tracks if you wanted this accessibility.
The labels and Apple will make a minute amount from this $25 fee. It will not even make a dent in the losses from piracy, but it will be SOMETHING. As I stated earlier, I only question how opting out will be handled. I assume that, since you will download the iTunes version of your ripped music at some point, you now simply own that replacement copy. If you opt out, you will just no longer have the ability to match any new/remaining songs. But that remains to be seen until the service goes live.
But you are right in your “license model” point. We are already there. When you buy a digital track, you are not buying a physical item. Therefore, you are simply buying a license to use that virtual item. As long as I am paying the flat rate (be that .99 or $1.29), I do not have an issue with it. If it ever trends toward your Brown Suger example (and I do NOT see that ever being the case for individual use…maybe for commercial), I will quickly stop buying digital music.
I’m glad they’re finally addressing notifications, but now that we have all of this inter-device syncing going on, hopefully they’ll fix the issue where you acknowledge a notification on say, your iPhone, only to be reminded of it again when you pick up your iPad.
iMessages, wireless sync and OTA updates sound interesting as well.
Some of the features of iCloud sound promising but after two years of MobileMe, call me skeptical.
And while we’re on the subject, how do my fellow MM subscribers feel about having paid for a service that Apple will now provide free of charge? I suppose we (and our data) were the beta testers for iCloud, huh? And wasn’t that a kick in the nads, the way they showed their appreciation by extending our subscriptions out to next June? So Steve, pray tell what is it exactly that we’ll be getting between now and when our subscriptions expire that iCloud users won’t be getting for free?
What I found most interesting was within the first minute of Steve Jobs talking about iCloud, an image appeared with none other than the current iPod Classic. Maybe a sign of things to come?
It all looks interesting but I hope Apple remember we don’t all have super fast pipes to our house and that in Europe you can’t travel that far without incurring the dreaded data roaming fees.
Also why do people get excited about notifications systems like the new one showing the weather where they are for that day, can’t they bloody look out of the window 😉
No Flash, No Cash
iTunes Match:
It was stated that once a music file is matched it will be treated as if you purchased it from iTunes. I’m interested to know how this will work? Will it be enough to have an MP3 with metadata? Or will it use Shazam-like technology to identify the song? What would prevent someone from creating a recording from radio and have it identified by iTunes Match?
I’m very excited about the new features of iCloud, lion & iOS 5. I’m looking forward to integrating them all to each of my devices. Its beginning to feel like what more can Apple & the developers add to keep their products ahead of the game?
Very confused about how the Cloud auto-sync will behave with multiple family members sharing one iTunes account. MobileMe family users weren’t mentioned at all regarding a transition to the cloud. I really don’t know haw they’ll handle it but I know there are a lot of people in the same boat.
Looks interesting, but what i want to mknow is will I be able to update my smart playlists from the cloud or not?
Unless there’s some sort of management and user profiles implemented, the whole “cloud” thing for music is a wide miss for me. I’m already managing three separate media libraries in my household, with three different sets of smartlists and syncing options, and pretty sure as my son gets older, that’s going to increase to four separate media libraries. There are different ratings, different metadata in the comments fields, different ratings, tweaks to naming conventions, etc.. Ignoring the “there’s no limit to the amount of songs… (oops don’t read the small print, it’s really 25,000)” matter, I just don’t see how this is remotely useful for families. Never mind the mess of picking and choosing from a total library for someone who doesn’t want 100% of everything tied to the family’s iTunes account information. Really, unless there are features they haven’t announced, this is little more than a clumsy online backup system, and for $25/year, I can just as easily buy another hard drive every other year and accomplish exactly the same service.
Now, if Apple can give us individual library management “in the cloud” while being tied to a family account and mirror metadata correctly, I will be all about signing up for the service, but it it’s just a bulk “free download” from an unorganized (by my standards ;-)) service, I’ll stick to my non-cloud setup where everything is organized to the individual.
I like the way that Jobs and Apple are thinking about computers, laptops and tablets. While people have been engaging in a false debate over whether the iPad could replace a laptop, Jobs simply and rightly declares, “We’re going to demote the PC and the Mac to just be a device — just like an iPad, an iPhone or an iPod Touch.” This just makes sense because it is possible that many types of work projects might originate or be edited or completed on any of these devices. So it’s not about which device is more powerful, it’s about access, when you want it and how you want it.
So for me the Cloud announcement is just a start. For example, I am more interested in being able to store or access video content on the Cloud as opposed to all of my music collection. But I look forward to being able to store information about purchases there, especially apps. I also look forward to being able to not having to sync an iPad or iPhone to a desktop or laptop.
It will be interesting to see how developers respond to the new tools they have to play with.
Personally, I love – and always have – loved Apple. I kinda think we tend to get too greedy with all that we ask for in the world of technology. (And, yeah, I’m expecting comments in response to that. That’s fine.) But we have to remember that nothing in life is perfect, but Apple does a reallllly freakin’ good job at making amazing products. Sure, they have to work out a few kinks, but overall, they have stellar products. I had an Android phone – one of the highest-rated ones, too – and recently switched to an iPhone because the Droid made me want to drive over the dang thing with a Hummer on a daily basis. I wouldn’t go back to Android unless they took some major steps up. That’s how much of an improvement in quality I’ve noticed with the iPhone, even with it lacking some of the cooler features the Android OS has going for it. So, I guess in a nutshell, I’m just saying we should cut Apple some slack with things and appreciate the amazing technology they’ve brought into our lives. ‘Nuff said.
By bulk download, I meant what you said: it has every single track (within its limits) as a big iTunes store like list, which sticks every single person having to pick and choose from that list to gain any utility from the service.
For the 20 y.o. who has no s.o. or children and can’t be bothered to back things up and has all their metadata at whatever the ripper entered it as, hey, genius new service. For the organized media HOH, very underwhelming when the latent coder in me sees how easy it would have been to do this right since the infrastructure is already there.
Maybe next year 😀
It starts. $25/year “fee” split with the record companies to listen to music I already bought. The music industry is slowing moving us all to a license model for music, since buying a “hard copy” CD is becoming less common.
Putting all my music in iCloud is a first step at the music industry claiming back every thing I “own”. Years from today, I imagine paying the estate of Mick Jagger and its record label $0.01 ever time I play Brown Sugar.
i love it and everything about the new operating system, it would be better if it came out eariler.
@drakebullet – I honestly think you are looking at this all wrong. Apple is not charging you one penny to listen to music you already bought. Sync it and listen to it. Apple and the labels are charging a pretty nominal fee to make that music universally accessible. They are charging for the convenience of having “reach back” capability to reacquire that music at any time and from any compatible device.
I have roughly 800 CD’s that I ripped into MP3 or AAC format so that I could load them onto my first iPod. I have since stopped buying CD’s and moved on to digital downloads (iTunes, Amazon, etc.) because the few CD’s I did still buy got ripped and quickly stored away. Why eat up valuable real estate with items that I would rarely (if ever) touch again? Now this iTunes in iCloud is going to let me access EVERY track from almost ANYWHERE. This matching is simply a way for Apple to make these tracks available with the least amount of effort on both ends. They simply have to create aliases under your account that point to the already existing digital tracks on their servers. That saves them storage space and you bandwidth AND time needed to upload all your tracks if you wanted this accessibility.
The labels and Apple will make a minute amount from this $25 fee. It will not even make a dent in the losses from piracy, but it will be SOMETHING. As I stated earlier, I only question how opting out will be handled. I assume that, since you will download the iTunes version of your ripped music at some point, you now simply own that replacement copy. If you opt out, you will just no longer have the ability to match any new/remaining songs. But that remains to be seen until the service goes live.
But you are right in your “license model” point. We are already there. When you buy a digital track, you are not buying a physical item. Therefore, you are simply buying a license to use that virtual item. As long as I am paying the flat rate (be that .99 or $1.29), I do not have an issue with it. If it ever trends toward your Brown Suger example (and I do NOT see that ever being the case for individual use…maybe for commercial), I will quickly stop buying digital music.
I’m glad they’re finally addressing notifications, but now that we have all of this inter-device syncing going on, hopefully they’ll fix the issue where you acknowledge a notification on say, your iPhone, only to be reminded of it again when you pick up your iPad.
iMessages, wireless sync and OTA updates sound interesting as well.
Some of the features of iCloud sound promising but after two years of MobileMe, call me skeptical.
And while we’re on the subject, how do my fellow MM subscribers feel about having paid for a service that Apple will now provide free of charge? I suppose we (and our data) were the beta testers for iCloud, huh? And wasn’t that a kick in the nads, the way they showed their appreciation by extending our subscriptions out to next June? So Steve, pray tell what is it exactly that we’ll be getting between now and when our subscriptions expire that iCloud users won’t be getting for free?
I dunno. Mac user since 1985, and this time things seems different…
When they (Apple) dumped the floppy – I was 100% on board.
When Apple dumped SCSI and we saw Firewire, I was also sold.
It’s been that way for many things Apple. iOS5 sounds great. It’s obvious where the focus at Apple is today.
However, as a Mac person, I don’t get the same warm, fuzzies. Lion looks a lot about GUI changes, and little more. A nice feature here and there, but overall, underwhelming…
Does this mean anything? Or is it just that THIS WWDC is about iOS and the cloud? Time will tell.
I hope that we get notifications when our apps are automatically updated, so I can click on the notification and see what changes were made to the app. That would be cool. Overall, I’m excited about these announcements.
No Flash, No Cash
Looks interesting, but what i want to mknow is will I be able to update my smart playlists from the cloud or not?
Unless there’s some sort of management and user profiles implemented, the whole “cloud” thing for music is a wide miss for me. I’m already managing three separate media libraries in my household, with three different sets of smartlists and syncing options, and pretty sure as my son gets older, that’s going to increase to four separate media libraries. There are different ratings, different metadata in the comments fields, different ratings, tweaks to naming conventions, etc.. Ignoring the “there’s no limit to the amount of songs… (oops don’t read the small print, it’s really 25,000)” matter, I just don’t see how this is remotely useful for families. Never mind the mess of picking and choosing from a total library for someone who doesn’t want 100% of everything tied to the family’s iTunes account information. Really, unless there are features they haven’t announced, this is little more than a clumsy online backup system, and for $25/year, I can just as easily buy another hard drive every other year and accomplish exactly the same service.
Now, if Apple can give us individual library management “in the cloud” while being tied to a family account and mirror metadata correctly, I will be all about signing up for the service, but it it’s just a bulk “free download” from an unorganized (by my standards ;-)) service, I’ll stick to my non-cloud setup where everything is organized to the individual.
Personally, I love – and always have – loved Apple. I kinda think we tend to get too greedy with all that we ask for in the world of technology. (And, yeah, I’m expecting comments in response to that. That’s fine.) But we have to remember that nothing in life is perfect, but Apple does a reallllly freakin’ good job at making amazing products. Sure, they have to work out a few kinks, but overall, they have stellar products. I had an Android phone – one of the highest-rated ones, too – and recently switched to an iPhone because the Droid made me want to drive over the dang thing with a Hummer on a daily basis. I wouldn’t go back to Android unless they took some major steps up. That’s how much of an improvement in quality I’ve noticed with the iPhone, even with it lacking some of the cooler features the Android OS has going for it. So, I guess in a nutshell, I’m just saying we should cut Apple some slack with things and appreciate the amazing technology they’ve brought into our lives. ‘Nuff said.
@Code Monkey (#37): Actually, it’s not even anything quite as sophisticated as a “bulk download” service.
iTunes in the Cloud right now is only going to do two things, neither of which have anything directly to do with the iTunes library on your PC:
1. Let you view and download previously purchased music on a per-account basis, on demand. You will need to sign into the specific account where you’ve purchased the music in order to see it and download it.
2. Provide the option to automatically download any new songs purchased on another device with the same iTunes Store account.
The first option is actually not all that different from what users have been able to do with Apps since the very beginning of the App Store three years ago. The only difference is that now it applies to music as well as apps, you’ll have access to an on-device searchable/browsable purchase history, and you don’t have to guess whether you’ve already bought something before hitting the “Buy” button (there won’t even be a “Buy” button, but rather an iCloud download button).
The second option is designed to handle only new purchases from the iTunes Store — AFAIK it does not apply to iTunes Match service (for your own music) at all. Basically, everything that’s in your iTunes Store account before you turn on iCloud will be available on-demand for download to any of your devices, but won’t be delivered automatically. Once you turn on iCloud, you will be able to decide, on a per-device basis, which devices receive your new purchases automatically.
I don’t expect any other library organization will come into play for the actual iCloud service, which seems like it will have no concept of playlists, metadata or organization beyond what is already in the tracks themselves (title, album, artist, etc). You’re not actually storing any of your own data in the cloud beyond a list of what you’ve purchased and/or matched. The actual content itself just comes from the great bit iTunes Store library in the sky.
That said, iOS 5 will also introduce Wi-Fi sync with iTunes, but this is strictly a replacement for USB sync and will only work over a local Wi-Fi network. This has nothing to do with iCloud (although I can se the Wi-Fi sync eventually extending to work through iCloud in the future).
By bulk download, I meant what you said: it has every single track (within its limits) as a big iTunes store like list, which sticks every single person having to pick and choose from that list to gain any utility from the service.
For the 20 y.o. who has no s.o. or children and can’t be bothered to back things up and has all their metadata at whatever the ripper entered it as, hey, genius new service. For the organized media HOH, very underwhelming when the latent coder in me sees how easy it would have been to do this right since the infrastructure is already there.
Maybe next year 😀
I dunno. Mac user since 1985, and this time things seems different…
When they (Apple) dumped the floppy – I was 100% on board.
When Apple dumped SCSI and we saw Firewire, I was also sold.
It’s been that way for many things Apple. iOS5 sounds great. It’s obvious where the focus at Apple is today.
However, as a Mac person, I don’t get the same warm, fuzzies. Lion looks a lot about GUI changes, and little more. A nice feature here and there, but overall, underwhelming…
Does this mean anything? Or is it just that THIS WWDC is about iOS and the cloud? Time will tell.
I hope that we get notifications when our apps are automatically updated, so I can click on the notification and see what changes were made to the app. That would be cool. Overall, I’m excited about these announcements.
I’m very excited for iOS5, and very intrigued by iCloud. The iOS Messenger looks really cool, as a ton of friends and family have bought iPhones recently. Heck, with all the cool features in the new firmware, I think I will go get an iPhone! I had sold my iPhone to finance my iPad, but now my wife needs a new iPhone (she still uses a 1st Gen!), so I think I will get a pair of em!
iCloud looks cool. I like the idea of having all of my important data backed up daily, so if I have to restore, or worse lose my iPhone, I can just restore from yesterday’s backup and it would be like nothing happened- pretty neat. This whole iTunes Match thing I still don’t fully understand, but I think I may look into it. Problem is, I prefer 320kbps, not 256… I am by no means an audiophile, but I think I can discern between the two..
All in all, each feature by itself isn’t necessarily ground-breaking, but all together they put a crap ton of polish on the system. My only concern is that my iPad 1G already has issues with memory with not a lot installed. With SBSettings by BigBoss (yes, it’s a Jailbreak tweak) I am able to see my available RAM, and let me tell you, it’s not good. This is why (or at least most of the time it is) heavy apps crash on iPad. Infinity Blade? Crashes all the time for me, because of no memory… With no apps open, I have at most 80-95MB of RAM available. To put that into perspective, an iPhone 4 or iPT4G will be in the 300MB’s range, sometimes more, sometimes a little less. So yeah, I don’t want iOS5 to do to my iPad what 4.0 did to the iPhone 3G… :-/
I’m very excited for iOS5, and very intrigued by iCloud. The iOS Messenger looks really cool, as a ton of friends and family have bought iPhones recently. Heck, with all the cool features in the new firmware, I think I will go get an iPhone! I had sold my iPhone to finance my iPad, but now my wife needs a new iPhone (she still uses a 1st Gen!), so I think I will get a pair of em!
iCloud looks cool. I like the idea of having all of my important data backed up daily, so if I have to restore, or worse lose my iPhone, I can just restore from yesterday’s backup and it would be like nothing happened- pretty neat. This whole iTunes Match thing I still don’t fully understand, but I think I may look into it. Problem is, I prefer 320kbps, not 256… I am by no means an audiophile, but I think I can discern between the two..
All in all, each feature by itself isn’t necessarily ground-breaking, but all together they put a crap ton of polish on the system. My only concern is that my iPad 1G already has issues with memory with not a lot installed. With SBSettings by BigBoss (yes, it’s a Jailbreak tweak) I am able to see my available RAM, and let me tell you, it’s not good. This is why (or at least most of the time it is) heavy apps crash on iPad. Infinity Blade? Crashes all the time for me, because of no memory… With no apps open, I have at most 80-95MB of RAM available. To put that into perspective, an iPhone 4 or iPT4G will be in the 300MB’s range, sometimes more, sometimes a little less. So yeah, I don’t want iOS5 to do to my iPad what 4.0 did to the iPhone 3G… :-/
Does it mean no NFC for IOS 5 / iphone 5?
Some interesting stuff. Wifi syncing? Thank God, finally! PC-less setup and updating? Awesome! iCloud backup (probably) fabulous (assuming it works, and there aren’t issues with multiple users with different sets of contacts on the same iTunes account…). Music match? If there were streaming from the cloud that would be awesome–I have way too much music to keep on my iPhone, so having access to all of it (which I do now through iSub access to my home computer) would be awesome, but with no streaming, it isn’t really worth that much to me. The notifications update is probably great, won’t really appreciate it until I use it. Kinda wish they’d just let the weather app or stock app or whatever update their icon for some of this stuff personally, but hey, its a start…
Does it mean no NFC for IOS 5 / iphone 5?
Oh it’s amazing how the Monday Morning Quarterbacks second guess, and the Saturday Night Coaches project…
I think that a lot of the things coming down the pike are VERY exciting. Some of the things don’t appeal directly to me, but unlike others I don’t actually expect Apple to spend their entire R&D budget on “What does Tory want in her Apple-sphere?”
The streaming, from what I’m understanding, is going to be similar to the old MP3.com where you could “upload” (although I think it will be a different access type) your music and if they had it available in their collection, by virtue of the labels allowing it, you could stream it elsewhere. As a teacher, I used to use this all the time for classroom atmosphere. I’m “hearing” that it will be high quality versions of the music, so even if you ripped at a lower quality you can stream it higher (depending on bandwidth). With the old MP3.com sometimes you couldn’t stream the entire album (even if you owned it) so it will be interesting to see how the service works. I’m not going to judge until I see it.
With the danger of sounding like I’m bragging, my music collection is HUGE (over 100GB). Like many, I’ve got music ripped from my original CD collections from the 80s and I still like to listen to it, so I do like the idea of being able listen to whatever I want whenever I want.
I’m thrilled with the notifications! Seriously seems like a small thing, but I am SO sick of watching something on Netflix and having “so and so is now following you on Twitter” pop up. Let me choose if I want to be notified or not!
I agree with #41. Even if everything isn’t out of the gate heaven on a plate, the fact is innovation doesn’t emerge from the head of Zeus like Athena…it comes out in dribs and drabs and takes lots of tweaks to become perfected…and then it starts all over again. I am thrilled to be a part of the generation experiencing it! I also often wonder if it isn’t more the chronologically “younger” generation whining more about things not living up to their pie in the sky expectatins. I STILL think my original Mac SE was magic in a little beige box, and have loved watching the growth from Apple (and other innovators) over the years!
As for whether someone else had it first, one of the things Apple does very well is make sure something just plain WORKS before implementing it. It may work BETTER down the line, but they don’t toss out something completely broken to see if it will fly. So someone somewhere created something first, second, or 33rd…who cares? I care that what I invest in works well for the majority of the things I need it to do, and concerns that are reasonable are addressed in a reasonable amount of time.
Oh it’s amazing how the Monday Morning Quarterbacks second guess, and the Saturday Night Coaches project…
I think that a lot of the things coming down the pike are VERY exciting. Some of the things don’t appeal directly to me, but unlike others I don’t actually expect Apple to spend their entire R&D budget on “What does Tory want in her Apple-sphere?”
The streaming, from what I’m understanding, is going to be similar to the old MP3.com where you could “upload” (although I think it will be a different access type) your music and if they had it available in their collection, by virtue of the labels allowing it, you could stream it elsewhere. As a teacher, I used to use this all the time for classroom atmosphere. I’m “hearing” that it will be high quality versions of the music, so even if you ripped at a lower quality you can stream it higher (depending on bandwidth). With the old MP3.com sometimes you couldn’t stream the entire album (even if you owned it) so it will be interesting to see how the service works. I’m not going to judge until I see it.
With the danger of sounding like I’m bragging, my music collection is HUGE (over 100GB). Like many, I’ve got music ripped from my original CD collections from the 80s and I still like to listen to it, so I do like the idea of being able listen to whatever I want whenever I want.
I’m thrilled with the notifications! Seriously seems like a small thing, but I am SO sick of watching something on Netflix and having “so and so is now following you on Twitter” pop up. Let me choose if I want to be notified or not!
I agree with #41. Even if everything isn’t out of the gate heaven on a plate, the fact is innovation doesn’t emerge from the head of Zeus like Athena…it comes out in dribs and drabs and takes lots of tweaks to become perfected…and then it starts all over again. I am thrilled to be a part of the generation experiencing it! I also often wonder if it isn’t more the chronologically “younger” generation whining more about things not living up to their pie in the sky expectatins. I STILL think my original Mac SE was magic in a little beige box, and have loved watching the growth from Apple (and other innovators) over the years!
As for whether someone else had it first, one of the things Apple does very well is make sure something just plain WORKS before implementing it. It may work BETTER down the line, but they don’t toss out something completely broken to see if it will fly. So someone somewhere created something first, second, or 33rd…who cares? I care that what I invest in works well for the majority of the things I need it to do, and concerns that are reasonable are addressed in a reasonable amount of time.
@Code Monkey (#37): Actually, it’s not even anything quite as sophisticated as a “bulk download” service.
iTunes in the Cloud right now is only going to do two things, neither of which have anything directly to do with the iTunes library on your PC:
1. Let you view and download previously purchased music on a per-account basis, on demand. You will need to sign into the specific account where you’ve purchased the music in order to see it and download it.
2. Provide the option to automatically download any new songs purchased on another device with the same iTunes Store account.
The first option is actually not all that different from what users have been able to do with Apps since the very beginning of the App Store three years ago. The only difference is that now it applies to music as well as apps, you’ll have access to an on-device searchable/browsable purchase history, and you don’t have to guess whether you’ve already bought something before hitting the “Buy” button (there won’t even be a “Buy” button, but rather an iCloud download button).
The second option is designed to handle only new purchases from the iTunes Store — AFAIK it does not apply to iTunes Match service (for your own music) at all. Basically, everything that’s in your iTunes Store account before you turn on iCloud will be available on-demand for download to any of your devices, but won’t be delivered automatically. Once you turn on iCloud, you will be able to decide, on a per-device basis, which devices receive your new purchases automatically.
I don’t expect any other library organization will come into play for the actual iCloud service, which seems like it will have no concept of playlists, metadata or organization beyond what is already in the tracks themselves (title, album, artist, etc). You’re not actually storing any of your own data in the cloud beyond a list of what you’ve purchased and/or matched. The actual content itself just comes from the great bit iTunes Store library in the sky.
That said, iOS 5 will also introduce Wi-Fi sync with iTunes, but this is strictly a replacement for USB sync and will only work over a local Wi-Fi network. This has nothing to do with iCloud (although I can se the Wi-Fi sync eventually extending to work through iCloud in the future).
Some interesting stuff. Wifi syncing? Thank God, finally! PC-less setup and updating? Awesome! iCloud backup (probably) fabulous (assuming it works, and there aren’t issues with multiple users with different sets of contacts on the same iTunes account…). Music match? If there were streaming from the cloud that would be awesome–I have way too much music to keep on my iPhone, so having access to all of it (which I do now through iSub access to my home computer) would be awesome, but with no streaming, it isn’t really worth that much to me. The notifications update is probably great, won’t really appreciate it until I use it. Kinda wish they’d just let the weather app or stock app or whatever update their icon for some of this stuff personally, but hey, its a start…