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.
For what it’s worth, I usually install Ubuntu Server instead of Debian because it comes with a few more things out-of-the-box that I would install anyway. I have several installations of 22.04 that have been upgraded since 16.04 and they work no problem. (I also have a few Debian installations working similarly well.)