Every once in a while, a reader suggests that Apple should offer wireless, over-the-air updates for iPhones—new iOS versions pushed directly over the cellular network without any need for iTunes synchronization. Sounds great, right? No need for a pesky USB cable or computer running iTunes. It all “just happens” and “just works.” But in reality, despite Apple’s best intentions, it probably wouldn’t go that way.

Instead, picture this:

Apple announces the release of iOS 5, but instead of announcing a specific release date as it has done in the past, Steve Jobs gets up on stage and simply says something like, “iOS 5 will magically appear on your iPhone or iPad with 3G in the next few weeks.” He offers no release date, no specifics, just a generic “coming soon” statement.

Fast forward a few days. A handful of users report that they’ve just received the latest and greatest iOS 5 update. You try iTunes’ “Check for Updates” button, but are told that iOS 4.3.3 is the most current version. You shrug and assume that the iTunes servers are just busy and that it will show up soon.

Later that day, a friend shows you all of the new features in iOS 5 on his iPhone from the update he just received through iTunes. You rush home, plug in your iPhone, hit the “Check for Updates” button again, and get the same response: iOS 4.3.3 is current. So Apple’s servers must still be busy, you figure, grumbling in frustration. At this point, you decide to give up and try again tomorrow.

Then a week goes by, filled with repeated attempts to update your iPhone. iTunes continues to insist that you have the latest version available, despite the fact that it seems everybody around you already has the update and you’ve been left out in the cold. You do a bit of digging online and find a few blog posts and discussion forums with people who are having similar issues. You quickly discover that the problem is not that Apple’s servers are merely busy, but that Apple has decided to do a staggered rollout of iOS 5, and you simply have to assume that your device is not yet one of the “chosen” to receive the update.

Finally, perhaps two to three weeks later, after you’ve already given up in frustration, iTunes suddenly pops up a message letting you know that it’s your turn, and iOS 5 is now ready to download for your device.

If this seems absurd and impossible… it’s not. This is exactly how things work with Android. And it suggests just some of the sorts of challenges Apple would need to work around in order to wirelessly update iOS devices.

Leaving aside the obvious issues with different hardware platforms and carriers, when Google chooses to roll out an update even to its own “chosen” Nexus reference device the process is an indeterminate and frustrating mess. Specific release dates are almost never announced in advance, leaving things vague. Meanwhile, discussion groups fill up with frustrated comments wondering when their specific device is going to receive the update. When someone from Google does surface to respond, it’s usually on the day that the rollout has begun, stating that the release is in the process of being rolled out and everybody should be getting it “in the next few days or weeks.”

Eventually, somebody posts a manual link to download the firmware for users who have grown tired of waiting for their device to become one of the “chosen” to receive the over-the-air (OTA) update. Since Google doesn’t provide this link itself, users question whether what they’re getting is really the actual and proper OS update, particularly in the Android world where modified ROMs and firmware packages are commonplace.

Getting the latest Android OS update is pretty much a game of “hurry up and wait” — even among users of the exact same hardware.

The problem is even further exacerbated by the fact that there are multiple versions of the Nexus S (and Nexus One) available, and it seems that the AWS version (for T-Mobile US, Wind Canada, and Mobilicity Canada) always receives the update weeks before the other GSM version used by major carriers AT&T, Rogers, Bell and Telus. This happened last year with the Nexus One and is now happening again with the Nexus S. While it’s reasonable to accept that there are subtle hardware differences between the two models, and that Google may want to roll out the software to smaller players before doing so with a larger user base, this distinction is lost on most end users. A GSM phone should be a GSM phone. An update should be an update for everyone. Right?

Yes, you could applaud Google for getting updates out as soon as it can, but it would probably create far less user frustration for Google to release an update when it’s ready for everybody, and then to actually release it for everybody at the same time rather than staggering wireless distributions. This leaves users wondering what day their devices will finally be chosen by Google. Of course, coordinating a simultaneous launch to update everyone at once would be challenging, and arguably perceived as more of a marketing or PR move than technically necessary for a software rollout. Google is a company run by engineers. And like many other engineering-driven companies, it doesn’t properly consider the social aspect—how left-out, frustrated users might feel over a period of days or weeks—and over time, those sorts of feelings lead to defections. Probably to the iPhone.

To be fair, the typical Android or iOS user may not pay much attention to upgrades, and therefore might just be pleasantly surprised when a new update does appear. For the power user, however, the “when am I getting this?” situation can be frustrating, and lends credence to the idea that Android remains a platform for the nerd-slash-developer crowd. Should Apple offer iOS users wireless, over-the-air updates? Only if and when it has solved the distribution problems Google and others appear not to fully understand or care about. By pushing upgrades through iTunes to almost all of its iOS devices at the same time, it’s already doing better by users than supposedly more advanced competitors. My guess is that it won’t abandon a model that works until it has something that works better for everyone.