Thank you for sharing your experience. It has so far been helpful.
New Mac user.
Devices used: iPod, MacbookPro. My iTunes libraries are 50/50 purchases/cd uploads.
See "*main goal*" at end for summary.
Here's the details of my specific situation:
1) Between '00 and '03 got an iPod (iPod_1) and set up iTunes account (iTunes_1) on a Windows PC (pc_1) using an email account (email_1).
2) Got new iPod (iPod_2) around '09. (details are foggy)
- It's possible that I plugged iPod_2 into a new PC (pc_2), set up a new iTunes account (iTunes_2) with @domain.com email (email_2), and then tried to physically transfer my iTunes_1 library to merge with iTunes_2 library. I remember this not working very well, but that's a side issue.
- Again, forgot email_2, but I have a list of possibilities to try.
3) Got a Macbook (pc_3) in 2014.
***Main Goal***
If possible, I would like to know how to access iTunes_1 and iTunes_2 libraries from pc_3 so that I can download purchases and cd uploads onto iPod_2. As long as I can download, I don't care how many accounts I have to keep track of.
If you could please explain how to do the following or refer me to the appropriate posts/websites, that would be great!:
1) How to verify emails used to create past iTunes accounts (iTunes_1 and iTunes_2). Also, if email no longer exists, what then?
2) How to set up iPod_2 so it recognizes or permits downloads from all three iTunes accounts. Or if impossible, other ways to get all content onto iPod_2.
3) How to configure Sync to prevent iTunes_1 (originally associated with iPod_1) from overwriting iPod_2, and vice versa.