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Thanks for this awesome write-up.
Yeah, that's what I'm kind of thinking about Cloudflare, so I'm trying to set up WireGuard right now. I don't know if I'm shooting myself in the foot by trying to do in docker for now or not, but I'd rather do that before I do it on bare metal. It seems to work already, as I can see that my IP changes on my phone when I access it. Hell, I can even access my routers' dashboard. However, I still can't access the services on the server (by IP, like 192.x.x.x:8989), so I'm trying to figure that out.
May I ask, why do I need a domain if I'm going through WireGuard, which goes through the IP and port, anyway?
Before you invest a lot of time into this just wanted to say that it's a 2m job with Tailscale. You install it on the server and on your phone (or laptop whatever), you start it, and you can access anything on the server at a short name you can customize fully, or at a long name you can pick from randomly generated choices generated by Tailscale. (The long name is usually only relevant if you're going to expose your server to the internet or in unusual DNS setups, if you just want to access the server from your phone the short name will do.)
OP's list is great for learning and for full control but if you just want to solve your problem fast, you can.
I’m either lucky or it’s stupid easy to install wireguard. I put basic config in docker compose, downloaded the app, port forwarded and I’m good. Even pihole works. It’d haven taken me 5 mins if it wasn’t for the firewall
One of the other benefits of Tailscale is device management. Wireguard is an awesome tool (Tailscale uses it under the hood), but adding new devices is more work with Wireguard, as you have to generate keys and share the public keys (and do some IP management). With Tailscale it's pretty much install the app and allow the device with a click.