Comment by jajuuka

It's not super difficult if you have an Apple ID from many years ago that you bought media with and then have a different Apple ID that you use for everything. Which isn't that uncommon for anyone who used iTunes and bought music or media and then forgot their ID and just made a new one when they got a iPhone or Macbook. Was able to transfer all my purchases to my main account pretty easily.

The real downside is if you have two fully active Apple IDs. Then things like calendars, photos, email, etc are still stuck on the other account until you export it. Which can be a pain since you have to sign out of your main account, sign into the old account and export, then sign back into the main account.