A giant clusterfk of poorly designed, non-intuitive, frustrating systems that did unexpected things or took too much time to set up

That sounds heavily under engineered, not the other way around.

What does VPN hide that HTTPS can’t hide for media server?

HTTPS Doesn’t hide where the traffic is going, so your ISP will track you going to piracy sites. It also doesn’t protect you against identification when torrenting.

Dude, read the rules #2 says no requesting invites