My first iPod was a first gen Shuffle. My best friend had a U2 iPod and I thought it was so cool. Since I'm vision impaired though, I thought there would be no way I could use the click wheel with its menus. So the Shuffle seemed in theory to be perfect since it had no screen. So I bought one when something I was working toward ended up not working out. I loved that thing even with only being able to load a small number of songs onto it.
Then I got a 5th gen classic for Christmas that year and loved being able to have my entire library whereever I went despite the lack of accessibility making it a guessing game if I wanted to listen to a specific album or song.
I sold it and switched to a new Windows Mobile device I got that had a full screen reader, but syncing that with Windows Media Player 11 made me dearly miss iTunes.
Then in 2008 my favorite iPod, the fourth gen Nano, came out. That was one of the rare times when I had to have a new piece of tech day one. That was when Apple started to up its commitment to accessibility. Before then, iTunes on Windows could only be made useable by a blind person if you bought a $75-100 plug in to use with one screen reading program, which I had and loved. Now, iTunes started to be more useable out of the box. I suppose those early Nanos weren't powerful enough for a full screen reader, so iTunes could generate voice recordings of the names of your music and the iPod's menus. You could do something similar with Rock Box on some earlier iPods before that, but Apple implementing it into the Nano's firmware was just better. It wasn't perfect though -- sometimes some of the voice tags wouldn't copy over so you would have to resync, and they took up part of the storage space. Even so, I loved that little blue guy! Many a day was spent walking around my college campus with it clipped to my pocket and earbuds in my ears. I wish I'd held onto it in retrospect.
I got a third gen Touch for Christmas in 2009. I would've happily kept using my nano, but by then VoiceOver had made its way to the iPhone and the Touch, and I wanted to try it. VoiceOver didn't come to the Nano till the sixth gen the following year. I would've snapped one up had it been out then though. That iPod Touch obviously lead to several iPhones later. starting with a used jailbroken 3GS that I sold the Touch to pay for in 2011, then a 4S, 5S, OG SE, XR, and now my current 12 mini.
RIP iPod era indeed.