I’ve honestly never tried it, since I have the only node in my home network serve the local subnet. It allowed me to statically assign IPs at home and still use them outside of the house. I suppose there’s nothing stopping you from using the overlay network, especially if you have all devices involved on the Tailscale network, but I didn’t feel like doing that :)
Something that might help with using Tailscale and reverse proxying: you don’t have to use the IPs given to you through the tailnet if you don’t want to. Something tailnet nodes can do is serve the local subnet theyre connected to, even if you’re running the self hosted version Headscale, which is what I do. This is how I am able to have my phone and one other pc connected through Headscale/Tailscale, but still access everything on my local network.
Im assuming your Jellyfin is on your local network, and you want to connect to it through Tailscale, but still use HTTPS? If that’s the case, you don’t need to do any kind of port forwarding on your router, as everything is funneled through Tailscale anyway.
I switched from windows 10 to Kubuntu a few months ago, and I’ve loved the freedom so far! Gaming has mostly been a non-issue, except for the 1 or 2 that won’t work due to anticheat nonsense. I have a debloated windows instance that I keep on a separate drive, and I’ve booted that POS maybe 2 times so far.
I got curious and tried Linux Mint and OpenSUSE, but ended back with Kubuntu because I prefer KDE Plasma and im most familiar with Ubuntu.
Be careful though, once you fall into the rabbit hole you’ll start doing things like run your own music server (like navidrome), and hosting your own photo storage server (I’ve tried both Immich and Photoprism).
Seconding Beszel, it’s dead simple to install, and add systems to. I love the sleek interface, and the ability to send notifications to a slew of services (like ntfy)