I got Jellyfin up and running, it's 10/10. I love this thing, and it reinvigorated my love for watching movies. So I decided to tackle all the other services I wanted, starting with Paperless-ngx...

What a nightmare. It doesn't have a Windows install so I made an Ubuntu VM. Don't get me started on Ubuntu. I just spent about 12hrs trying to get Portainer to cooperate and had to give up. I tried just installing Paperless the "normal way" and had to give up on that too.

My point: if you're getting started selfhosting you have to embrace and accept the self-inflicted punishment. Good luck everybody, I don't know if I can keep choosing to get disappointed.

Edit: good news! Almost everything I wanted to do is covered by Jellyfin which can be done in Windows.

Edit2: It's been a year, and a lot has changed. I'm currently running a NAS + Ubuntu server. I'm running over a dozen docker containers among other miscellaneous services, and these services are being used by close friends as well. I owe several people apologies for being so quick to dismiss the entire Linux community. I found a few mentors, and now I'm good. To anyone looking for help to get started, you're going to have a much better time in the long run if you join some help groups on Discord (I hate it, but it works).