I love Tailscale as well and it works flawlessly for everything I've ever used it for. However, I can't install Tailscale on the Roku TV that sits remotely from my server. That's the whole reason I'm looking for a different way.
I'm pretty sure that using Jellyfin over Cloudflare tunnels is against their TOS, just FYI. I'm trying to figure out an alternative myself right now because of that.
I was running Pi-hole on an actual Raspberry Pi 4 that was apparently running Raspbian 10. My upgrade did not go smoothly. But I got it and I'm liking the new version. The only issue I see so far is that the admin panel in v5 used to have a "remember me for 7 days" checkbox when logging in, this version does not.
When I type in my home address, it lists it in a city that's three towns away from where it is. Maps it in the correct location though. My address is correct and in the correct town in OpenStreetMap. That's enough for me to not use Organic Maps. I don't want to guess what incorrect town to use if I type in an address to navigate to.
Thanks for mentioning. I ended up using a Tailscale funnel and everything is running swimmingly so far.