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.