I do agree on that using LLMs to demistify, learn and explore is better alternative than handing it off to go rouge on, is a better advice. That's how I used it last weekend and I think that's what I would advocate the usage instead of just letting YourFavouriteAI be the sys admin.

My problem is not just networking knowledge. I genuinely faced issues with open source tools. Troubleshooting in the days of terrible search is also a major annoyance. Sometimes, it's just the case that some of the tools have evolved and the same commands don't work as did for someone in 2020 in some obscure forum. I remember those days of tinkering with linux and open source where you'd rely on a Samaritan (bless their soul) who said they'd go home and check up and update you.

Claude suggested me Tailscale too, but I'm glad we're having this conversation (thanks for the tips btw), so that we don't follow hallucinations or bad advice by similarly trained agents. I'm cautiously positive, but I think there's still a case to go self hosted with AI assistance. I found myself looking at possibilities rather than fearing dead ends and time black holes.