Selfhosted

This may be a controversial approach, but I recently had to set up reverse proxy along with DNS configuration and certificate handling. I pair programmed with an LLM.

My experience was this... I described what I wanted to set up, my objectives (like containerisation, zero touch deployment, idempotence, etc) and it gave me a starting point. It threw a few bad ideas in but I also asked it to help me stress test against the objectives. I think it's all just about working now. I learned a lot about shell, docker, nginx, terraform, VM metadata, data persistence, pulling it all in from a git repo, bootstrapping nginx with self-signed certificates, auto renewal, vscode devcontainers and more. Honestly I'm worried about what a pro would make of my code, but I made huge steps in a relatively short time. Disclaimer: I am a software engineer who was keen to learn this stuff and get moving quickly.

I would definitely consider this approach if you're new to the area.

I know this is beyond the scope of your question but you are at a very similar place like i was over a year ago.

For the reverse proxy you want ingnx manager and it will handle all of your reverse proxies just fine.

But what i really want to recommend is to change up that debian into proxmox,

Proxmox is a debian based efficient server OS. Basically every service you run now can Easily be run as its own isolated container with very little overhang.

Best of all there is a community for Helper script that will install entire services including Nginx but even nextcloud from a single command.

https://community-scripts.github.io/ProxmoxVE/scripts?id=nginxproxymanager

Caddy

It’s three lines of configuration

jellyfin.example.com {
  reverse_proxy http://localhost:8083/
}

Automatic https with let’sencrypt, simplicity of a single binary, downgrade is as simple as replace binary & restart service.