Thanks for the answers. I guess that was not clear from my post, but I do not want to expose anything to the internet. All I want to do is tidy up the urls to the services for clarity. I have no issue with installing Tailscale on every device I want to access my services with. I can currently access any service just fine by doing “tailscaleIP:PortOfService”, but that is kind of unpractical. So by using my domain and Cloudflare DNS I changed it to “mydomain.com:PortOfService” which is already better, but means I have to look up what port the service I need uses. Like I said in my post I’d ideally like “nameOfService.mydomain.com”, no ports. And yes I realize this is purely for convenience/aesthetic reasons. Apologies if my words are not clear enough.

Interesting, I am actually not using a reverse proxy, just Tailscale (or does that count as a reverse proxy?), I had previously been using nginx proxy manager but ditched that because it became too much of a hassle (and everyone says it’s not secure enough)

I meant streaming shows with Jellyfin works fine, so I don’t see why streaming music shouldn’t work at least as well. I don’t like using streaming clients such as Plex or Jellyfin for music, they just feel quite unpolished.

Depends, I get two problems, one where the song will abruptly stop playing at about the 1 quarter mark (only skipping the song or restarting will fix), and the other being the generally slow and unreliable streaming. The former happens everywhere, even in the webUI in my LAN, and the latter only when out and about (Tailscale into my network).