Can I transfer iTunes purchases to new iTunes account My wife has had her iTunes connected with her parents and sister's account since middle school.  She hasn't ever synced her iPhone 4 with iTunes in that time, but she wanted to upgrade to iOS 5 to be able to upgrade some apps (pinterest, I think).  We created a new iTunes account, and obviously now I can't sync her old songs and apps.  Does anyone have any suggestions on how to get all of these songs again?  She has thousands, so it is not feasible to burn them all to CD then rip them all again (in addition to the quality degradation), and I can't buy them all again.

Thanks,

Tim
It's obvious Apple has a build in procedure to block this kind of actions. Otherwise they would go bankrupt... (Haha :)) 

However there are some work-arounds:


eHow.com has dedicated a tutorial concerning this issue. I haven't tested it, but the intro states it will do what you've asked
another way to do so is to just use both account on your iTunes, iPhone, iPad,... I do it with my iPad as well (both US and Belgium account) and yes it's a hassle, but it does the trick. I can access the apps, music and more from both accounts.