Q: Through my family member’s iTunes Music Store accounts, and a few I’ve purchased on eBay, I seem to have exceeded a limit I never knew existed: my iPod will only accept songs from 5 of these accounts, refusing to synchronize songs from the others. Is there any way to get around this?
A: This is indeed a rather subtly-advertised limitation of the iPod/iTunes system. Similarly, an iPod can only synchronize Audible audiobooks from no more than two accounts simultaneously.
You can’t (legally, at least) get around this limitation at all. However, you can attempt to exert more control over which five accounts iTunes will synchronize; by default, iTunes chooses itself.
The trick is to manually disable the synchronization of the songs belonging to accounts you’d like to temporarily disable. One way to do this is to disable the synchronization of unchecked songs, and simply un-check the songs associated with your older accounts. You could also use the “Automatically update selected playlists only” mode, and ensure that the accounts you don’t want aren’t included in your selection. For more help, see our synchronization tutorial here.
Granted, this isn’t the solution you’re looking for, as the ultimate result will be that you’ll still be carrying less than all of the songs you’ve paid for. However, at least with this method, you’ll be able to choose what you have to leave behind.