I still use my 2006 iPod. It's a 5.5th generation model that came with an 80GB HDD and IIRC I paid $400 for it.
The battery eventually died. Replacements are about $8 and the surgery is easy.
What makes a huge difference though is replacing the HDD with a board that holds an SD card. The board plus a 256GB card cost me around $75 total. The physical swap is relatively simple, and migrating your data is as simple as making a backup through iTunes and restoring it.
I mostly leave it plugged into my car, which has native support for controlling it. Unlike anything Bluetooth, it actually works!
The car integration is an underrated aspect in my opinion.
I used to travel for work and would rent cars. I would spend 3+ mins after picking up each car trying to get my bluetooth to work with my phone until I realised I could just plug in an iPod (from 2005!!) into the USB port of a MY2018+ vehicle and have my entire music library accessible through the car's interface with artwork. Just plug it in, and it would just pick up where I left off, on the podcast/album I was listening to on the plane.
I now use a 16GB 6th gen Nano set to shuffle for all my music needs in my car. I got it cheap since the battery doesn't last that long but it's fine when plugged in all the time.
The battery eventually died. Replacements are about $8 and the surgery is easy.
What makes a huge difference though is replacing the HDD with a board that holds an SD card. The board plus a 256GB card cost me around $75 total. The physical swap is relatively simple, and migrating your data is as simple as making a backup through iTunes and restoring it.
I mostly leave it plugged into my car, which has native support for controlling it. Unlike anything Bluetooth, it actually works!
Oh, and I buy music on Bandcamp. Fuck streaming.