I suggest trying out this YouTube Music app. You can install a plugin from the app that will use yt-dlp and download from YouTube Music which gets you slightly better audio quality at 256kbps vs downloading from a YouTube video.
Wanted to say that I've used Rockbox on an old ipod classic with much success. Would recommend. You can even install user created apple-ipod-like themes to get closer to the original look N feel
I never got that feature of tailscale to work either, sorry. But, it was simple enough to share individual nodes to other users. So try that if it fits your needs.
Not OP, but thanks for sharing about headscale. I wasn't aware this existed. Probably won't make a switch to it anytime soon, personally. I have way too much connected on tailscale right now.
I suggest trying out this YouTube Music app. You can install a plugin from the app that will use yt-dlp and download from YouTube Music which gets you slightly better audio quality at 256kbps vs downloading from a YouTube video.