I had considered this. I still may at some point. I wanted to play with the original interface and experience that. Plus my car connects well to iPods (it’s an older car) and that’s pretty handy. I’m pretty sure it’ll get the audio from rockbox but less confident playlists and such will work.
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.
For me it’s also about reducing my reliance on my mobile. Teaching my kids by example that life isn’t only on my phone is easier when I can more clearly demonstrate what I’m doing. To listen to music I get my music device. When I want to take pictures, I grab my camera.