Pommes_für_dein_Balg

Time to switch distros!

Self-hosting on Windows Server is a pain I don’t need in my life.

Yes, Debian. It’s called the universal operating system for a reason.

To do this properly, you’ll need to set up a reverse proxy that publishes your different ports on different IP addresses.
Then you can use DNS or (locally) a hosts file for name resolution.

I’m not having any issues with my current setup

There’s your answer.