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.
Thanks for mentioning. I ended up using a Tailscale funnel and everything is running swimmingly so far.