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 get where you're coming from, really. I've been disappointed by Linux for years with the learning curve and random errors that no one can help with. I'd take a long break from anything server related and then once you think your ready to come back, go watch some videos that give you inspiration like Techno Tim. Try to make a game plan and stick to it. Use standard stuff like Debian and Proxmox for software and to get a head start try this. Wish you all the best mate.
People can help you, but there is a way to ask, and learning how to ask is part of learning the OS. We are fascinated by problems actually.
The problem is that people come and say things like "I tried to setup a fleegbat server and it doesn't work!" and so for the helper it becomes a process of pulling the information out of the asker in a long and painful process of interaction and we just move on. Users who say things like "here is the error message I'm getting when I try to start up my fleegbo server, anyone understand this?" get way better help.
Those who really want to learn it come to understand these things, those who just want to do something neat and not work their ass off will complain that it's too hard.
Those who do the work are rewarded in many ways. I drove a dump truck ten years ago, now I make twice what I used to, working with people who aren't racist sacks of shit. They were my motivator to learn, I was tired of being among pigs every day.
You nailed it, the problem is the problem with having to troubleshoot by yourself as a newbie. Once might not be an issue, but every step feels like a new instance of a repeat problem. Thanks for the encouragement