Syncing entire library
Bought a new computer and a new iPod, and wanted to sync my entire iTunes library. I guess that's possible, but not in the way I thought: you can sync to the entire library purchased from a particular machine, but not your entire library that I assumed was resident somewhere in the Apple cloud. So, if you have used more than one computer to buy iTunes, you can sync only to one fully, and then track-by-track for the other machines? In addition, having synced from one machine - about 2000 tunes - when I "transferred" these tunes from my new iPod to the new computer, only about 280 sings transferred. The message was that I have too many devices, but I had previously deauthorized all computers, and only reauthorized two, so not sure what's going on. I called Apple Support yesterday, but the person was not able to initialize her app to view my desktop, so we eventually decided to just give up for now.
iPod nano (7th generation, Mid 2015), most recent software on all machine