So I've been using Apple's services to some degree since just before the first iPhone. My original Apple ID is a .mac address and it's the account I've used on the iTunes/App/Mac App store ever since--is tied to every all apps, music, video, or Mac software I've ever purchased. Unfortunately, all of my cloud services are tied to a second Apple ID that was created with the release of MobileMe (ugh..), which has either a .me or .icloud address. My bookmarks, iCloud Drive, reminders, backups, keychain, and now photos are all tied to this address. The problem is that now that my kids are getting older, I'd like to have them each use their own Apple IDs for their own content and thus, would like to set up family sharing. The problem is that using either account causes headaches of a different variety. Use the .me account and it doesn't include any of the content bought to date. I don't know how much but considering it's been 8 years, it's a pretty significant chunk of change. If I use my older .mac address, I have the content but nothing else, including my keychain, backups, and photos. Any advice on best way to handle this? I'm guessing my only choice if I want to save my app purchase history is to use the older account and move what I can over from the .me account. My biggest concern presently is moving my photo library from one iCloud account to the other.