I find LLMs make a lot more.mistakes when they try to distill a guide down to steps. Its not a bad summary, but they to get confused sometimes when there are forks in the guide. That said they are really good at finding guides, especially older ones that SEs tend to not place as high

I think your best bet is to pick one thing that you can get a good guide for and start from there. If you really want to learn its probably better to start with a Debian or arch setup than proxmox, but that’s really going to depend on what you really care about learning.

I know it will be an unpopular opinion but you can use perplexity or Claude to help you find useful sources online if you’re striking out on your searching. Most of the time I find they do better with more obscure issues, but those should be rare if you’re following a guide

I tried out Komodo, but gave up on it. I looked at dockge after, but opted not to try it out. I prefer the IaaC setup with my compose in a repo for versioning and rollback. And while I think you can probably combine the two, komodo was getting in the way most of the time. It centered around secrets management and generating those secrets at run time.

That said, I feel like if I expand beyond a single server I may go back to one of these tools

I use wireguard directly instead of tailscale. Not sure what router you’re using, but mikrotik support it out of the box. I am sure they are not the only ones. My phone runs on it 24/7 and has access to the rest of my services.

I haven’t setup nextcloud, so can’t give any advice on that. Immich was insanely easy to setup though.

I like navidrome, but I am not using jellyfin, so I have nothing to compare it with.