I’ve been using a gen 5.5 for about 10 months and am quite enjoying it. I bought a refurb with a fresh battery and SD card replacement. Sounds great, nostalgia moments on point, and can enjoy music without my phone.
On Linux it’s been a bit cumbersome to get content on, and the podcast experience is subpar by modern expectations, but I still appreciate the tactile interface. It’s nice to interact with things that aren’t all glass touch surfaces.