Q: I have a new iPad 2. I have purchased music from the iTunes store and copied music from CDs that were downloaded from my home iBook. I wish to transfer them into my iTunes account on my work laptop. Can this be done without losing the music from the CDs?
A: Yes. There are several ways that you can go about this, but the basic task is to copy the music from your home computer over to the work laptop. You can either do this directly using an external hard drive, network connection, or optical media such as recordable CDs or DVDs, or you can use the iPad 2 as an intermediate device.
It sounds like in this case you’re dealing with a Mac at home and a Windows laptop at work, which makes the process a bit tricker, but still very doable. The problem is that iTunes stores full paths to every file in your library database, and because the file systems between Mac and Windows are fundamentally different, it’s impossible for it to directly reference these files on the new computer, which may result in broken links.
The solution in this case is to use the “Consolidate Files” option, which copies everything into the “iTunes Media” folder. You can that iTunes Media folder over to the new computer preserving it’s layout. When iTunes can’t find a track in its specific location, it will fall back to looking for it in the location where it would normally place it by default. If the file is in that location, as it would be after a “Consolidate” operation, iTunes will successfully find it and update the location to reflect its new Windows-based pathname.
This is all explained in much greater detail in our tutorial on Transferring your iTunes Library.
Alternatively, if you have all of the content on your iPad 2, you can simply copy it onto the work laptop from there. Purchased content can easily be transferred using the iTunes application, but you will need to rely on third-party tools to transfer the music you have ripped from your own CDs. See Copying Content from your iPod to your Computer for more information.