Caddy took an afternoon to figure out and setup, and it does your certs for you.

Unfortunately, I feel the same. As I observed from the commenters here, self-hosting that won't break seems very expensive and laborious.

Reverse proxy is actually super easy with nginx. I have an nginx server at the front of my server doing the reverse proxy and an Apache server hosting some of those applications being proxied.

Basically 3 main steps:

• Setup up the DNS with your hoster for each subdomain.

• Setup your router to port forward for each port.

• Setup nginx to do the proxy from each subdomain to each port.

DreamHost let's me manage all the records I want. I point them to the same IP as my server:

This is my config file:

server {
    listen 80;
    listen [::]:80;

    server_name photos.my_website_domain.net;

    location / {
        proxy_pass http://127.0.0.1:2342;
        include proxy_params;
    }
 }

 server {
    listen 80;
    listen [::]:80;

    server_name media.my_website_domain.net;

    location / {
        proxy_pass http://127.0.0.1:8096;
        include proxy_params;
    }
}

And then I have dockers running on those ports.

root@website:~$ sudo docker ps
CONTAINER ID   IMAGE                          COMMAND                  CREATED       STATUS       PORTS                                                      NAMES
e18157d11eda   photoprism/photoprism:latest   "/scripts/entrypoint…"   4 weeks ago   Up 4 weeks   0.0.0.0:2342->2342/tcp, :::2342->2342/tcp, 2442-2443/tcp   photoprism-photoprism-1
b44e8a6fbc01   mariadb:11                     "docker-entrypoint.s…"   4 weeks ago   Up 4 weeks   3306/tcp                                                   photoprism-mariadb-1

So if you go to photos.my_website_domain.net that will navigate the user to my_website_domain.net first. My nginx server will kick in and see you want the 'photos' path, and reroute you to basically http://my_website_domain.net:2342. My PhotoPrism server. So you could do http://my_website_domain.net:2342 or http://photos.my_website_domain.net. Either one works. The reverse proxy does the shortcut.

Hope that helps!