I daily drive an iPod (currently listening to it on a flight). Some benefits:
- Listening to music doesn't drain your phone. Also it's offline, which is a bonus for hiking/biking/flights.
- Underrated convo starter. Set one down on a bar top as you sit down and i promise you'll be talking to everyone around you
- The battery life is unmatched, including by modern DAP's. Mine is running a stock battery (still!) and gets days of playback. Weeks/months when idle (use it too much to know for sure).
- iFlash [1] has replacement boards for $30-$40 that let you use modern nvme storage over spinning media. Simple swap and has been rock solid for me for years.
- Audio quality over 3.5mm aux ports is noticeably superior to bluetooth in most (older?) cars
Would they take off today? I think there could be a retro-y scene for them, especially if they had any wifi connectivity. The device remains one of the best purpose-built consumer devices, and that's hard not to appreciate. My 10yr old daughter thinks it's less cool than i do, though.
Do you use some old version of iTunes to put music on it or are there other tools with better support for old iPods?
Original iPods (and early iPhones) weren’t locked down as much. There were a number of utils that could manage your library. ml_ipod plugin for WinAmp comes to mind.
All my music gets copied into OS X's Apple Music, which still supports iPods. Other repliees are arguably better alternatives these days.
on macOS you can still manage/sync iPods from the Finder (it was moved to there from iTunes when they killed iTunes).
Rockbox.