Jellyfin has Watch Groups that my (tech-challenged) family uses regularly without my help.
I just added IPTV to my setup, so I haven't tested if they work together. I can't see why they wouldn't. Worse case, have then tune into the same channel as you, it should sync up almost perfectly on its own.
If you want to PM me your docker-compose.yml and Caddyfile I'm more than happy to take a look at them for you. I've been using Caddy as my rev-proxy for 10+ app stacks for a few years now.
I recommend adding hostname: app-name lines for each container then you can just use the hostname and the native port (even if you don't pass it through with a port: line).
It's super useful if you want to expose any apps with a reverse proxy like Caddy. That way the ONLY way to access an apps web interface is via the reverse proxy. Then look at filter rules to deny access unless the client has a LAN IP.
Poof, you've got SSL and custom subdomains for all your apps, but still only on your LAN or personal VPN (like Wireguard or Tailscale).
I've been using Caddy instead of nginx for years now. As long as your port forwarding is already setup, it'll pull TLS certs for every domain in the config automatically and keep it up-to-date forever.
It's also super easy to use as a reverse proxy, so you can run one caddy server for all your sites on the same machine pretty easily.
It's unclear to me how this project does anything to protect the identity of users or who is talking to whom. It's nice to know my messages can't be read, but if my ISP can see who I'm talking to and how often it's not doing much.
Also how to clients find one another? Tor and i2p sites are notoriously require friends or public wikis to share the addresses.
Yeah, you'll need to spin up a Jellyfin server. It's really easy in docker though, and it shouldn't need a machine too powerful. I've heard of people running it on an rPi4 or old laptops.