I also tried tailscale in a docker container as a subnet handler and realized I was out of my depth. Net engineering is abstract and hard. There’s a reason there are pros making bank just doing that for big corps.
Followed a way simpler setup. Now tailscale runs on the server bare metal and podman handles the routing automatically. I just use the magicDNS address given by tailscale and everything just works as intended. All my services are available, and apps run no issue, no matter where I am as long as I’m connected to tailscale. I will make the setup more complex as I learn more and acquire the need for more features. But so far this has met all my expectations.












It sounds like you’re trying to do too much manual stuff. Anything self-hosted is rather complex by default. But, it is designed to be simple to manage and install, as long as you use the tools intended for it. Jellyfin is packaged in all sorts of ways, and each way aims at different use cases. If it’s going to run on your daily driver, best use docker to keep your desktop and the server separated, else it might complain of that sort of library compatibility issues.