The rm -rf comparison is a bit dramatic. WireGuard's config is conceptually simple: your key, peer's key, endpoint, what IPs route through the tunnel. The "implications" are minimal. It is a point-to-point encrypted tunnel.
Being overwhelmed by networking basics is worth addressing regardless. It comes up constantly: debugging connectivity, deployments, understanding why your app cannot reach a database. 30 minutes with the WireGuard docs would demystify it. The concepts are genuinely simple and worth 30 minutes to understand as it applies far beyond VPNs.
I have become pragmatic too. I do not tinker for the sake of it anymore. But there is a difference between choosing convenience and lacking foundational knowledge. One is a time tradeoff, the other is a gap that will bite you eventually.
And with LLMs, learning the basics is easier than ever. You can ask questions, get explanations, work through examples interactively. There is less excuse now to outsource or postpone foundational knowledge, not more[1].
At some point it is just wanting the benefits without the investment. That is not pragmatism, it is hoping the gaps never matter. They usually do.
[1] You can ask an LLM to do all of that for you and make it help you understand under less than 10 minutes!
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.
I am glad that it is useful to you! The "terrible search + outdated forum posts" problem is real for sure. LLMs genuinely help there by synthesizing across versions and explaining what changed.
I would say that self-hosting with AI assistance is the right approach. Use it to understand, not to blindly execute. Trust me, it is not much of a deal and you will be happy to have gone with this route afterwards!
Good luck with the setup. If you have any questions, let me know, I am always happy to help.
Being overwhelmed by networking basics is worth addressing regardless. It comes up constantly: debugging connectivity, deployments, understanding why your app cannot reach a database. 30 minutes with the WireGuard docs would demystify it. The concepts are genuinely simple and worth 30 minutes to understand as it applies far beyond VPNs.
I have become pragmatic too. I do not tinker for the sake of it anymore. But there is a difference between choosing convenience and lacking foundational knowledge. One is a time tradeoff, the other is a gap that will bite you eventually.
And with LLMs, learning the basics is easier than ever. You can ask questions, get explanations, work through examples interactively. There is less excuse now to outsource or postpone foundational knowledge, not more[1].
At some point it is just wanting the benefits without the investment. That is not pragmatism, it is hoping the gaps never matter. They usually do.
[1] You can ask an LLM to do all of that for you and make it help you understand under less than 10 minutes!