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.
I recently ditched Portainer entirely - it looks good, but when debugging anything it is really not helpful, often getting in the way. And if it runs on the first try I don't need a web interface.
My tips:
Run self hosted things on Linux and open their webpages on Windows if you really want or need to keep using Win.
Prefer docker compose "stacks" over docker directly or native installs. Personally, I just use 4 sub-commands for pretty much everything I do: up, down, pull and logs. You (probably) don't need Portainer.
If after 1. making sure the docker-compose.yaml is right, 2. setting up the .env file if present, and 3. following the instructions in their README; a container stack doesn't run after 2 or 3 attempts: copy the error message and search their GitHub issues - chances are someone else also faced that problem. If you can't find anything similar, open a new issue.