For your own personal items? It's not really worth it IMO. However if you're hosting something for the public, like a Lemmy server, then absolutely yes you should.

For Emby that is breaking their ToS, and you'll have a big corpo watching your traffic all the time. Just buy a cheap 5-10 dollar domain and get HTTPS up and running and you'll be fine.

This might help you understand things a little better. I would advise staying away from Cloudflare if you are self-hosting for privacy.

Quite clearly NO It is a central office that now answers a large part of the DNS questions; apart from the fact that they so often have failures.

Tailscale

Acronyms, initialisms, abbreviations, contractions, and other phrases which expand to something larger, that I've seen in this thread:

8 acronyms in this thread; the most compressed thread commented on today has 15 acronyms.

[Thread #318 for this sub, first seen 1st Dec 2023, 01:55] [FAQ] [Full list] [Contact] [Source code]

Skip Emby and look into setting up Jellyfin with Nginx proxy manager. At the end of the day, whatever solution you go with be sure to enable good password security or more advanced security options like 2FA for your exposed Jellyfin service.

You're asking on Lemmy, so you're going to get a lot of privacy related answers. For usability, Cloudflare tunnels are a super easy and free way to setup and don't involve your family members having to VPN into your network with Tailscale or Wireguard. This is especially useful if they are streaming from a smart TV or media stick.

Is it the most privacy-friendly? No. You're giving up a little bit of that for convenience and lower maintenance. IMO for my threat model, it's worth it.

I only use cloudflare for Home Assistant and Bitwarden, just not to have many layers where a problem could happen as those 2 services are critical.

I rent a VPS with Authentik and Wireguard for the rest, like Nextcloud, Emby etc. But it's huge hassle with ssl certificates, especially with Let's encrypt ones.

But honestly I've never used it, except the HA and Bitwarden. When I'm on vacation I just want to experience as much as I can from the location I'm at. And I'm trying to stay away from computers when I'm away. And my family really does not care about Emby. So I'll probably stop it.

And BTW you probably shouldn't pass video streams through cloudflare as it's against their TOS. Although I didn't hear about anyone who has been banned.

If you want simple and no hassle solution, just use Tailscale or ZeroTier.

You can use CF Tunnel so you don't need to expose any ports from your router. They'll also do SSL termination for you as well. You can use their free plan for this AFAIK. You can also run your own SSL proxy as well with HAProxy or Nginx. I'd just use CF, it's easier TBH.