Lots of people have been talking about products and tools. It’s docker, tailscale, cloudflare proxmox etc. These are important, but will likely come and go on a long enough timescale.

In terms of actual skills, there’s two that will dramatically decrease your headaches. Documention and backup planning. The problem with developing those skills is, to my knowledge, they’ve only ever been obtained through suffering. Trying to remember how to rebuild something when you built it 6 months ago is futile. Trying to recover borked data is brutal. There’s no fail-safe that you haven’t created, and there’s no history that you haven’t written. Fortunately, these are also the most transferable skills.

My advice is, jump in. Don’t hesitate. The chops in docker/linux/networking will come with use and familiarity. If it looks cool, do it. Make mistakes. You will rapidly realise what the problems with your set up are. You will gain knowledge in leaps and bounds from breaking a thing vs learning by rote or lesson. Reframe the headaches as a feature, not a bug - they’re highlighting holes in your understanding. They signpost the way to being a better tech, and a more stable production environment.

The greatest bit about self hosting for me is planning the next great leap forward, making it better, cleaner, more robust. Growing the confidence in your abilities to create a system you can trust. Honing your skills and toolset is the entirety of the excercise, so jump in, and don’t focus on any one thing to master or practice before hand!