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 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.