I actually think Tailscale may be an even bigger deal here than sysadmin help from Claude Code at al.
The biggest reason I had not to run a home server was security: I'm worried that I might fall behind on updates and end up compromised.
Tailscale dramatically reduces this risk, because I can so easily configure it so my own devices can talk to my home server from anywhere in the world without the risk of exposing any ports on it directly to the internet.
Being able to hit my home server directly from my iPhone via a tailnet no matter where in the world my iPhone might be is really cool.
Now I have tailscale on an old Kindle downloading epubs from a server running Copyparty. Its great!
Why did people use Dropbox instead of setting up their own FTP servers? Because it was easier.
I could, I just choose not to and direct my interests elsewhere. Those interests can change over time too. One day someone with Tailscale can decide to explore Wireguard. Similarly, someone who runs their own mail server might decide to move to a hosted solution and do something else. That's perfectly fine.
To me, this freedom of choice in software engineering is not disheartening. It's liberating and exciting.
Nobody said do everything from scratch. The point is: basic networking (port forwarding, WireGuard) should not be beyond someone's capability as a software engineer.
"I use apt instead of compiling" is a time tradeoff. "I can't configure a VPN" is a skill gap. These are not equivalent.
If you choose convenience for whatever reasons, that is completely fine.
The siloing of basic infrastructure knowledge into "not my discipline" is part of the problem. Software gets deployed somewhere: understanding ports, keys, and routing at a basic level is not specialized knowledge.
Honestly, if 10 lines of config is "network engineering", then the bar for software engineering has dropped considerably.
The 10 loc is not a valid measure.
`sudo rm -rf /` is a 1 line of code. It's not the lines that are hard to wrap your brain around, it's the implication of the lines that really what we are talking about.
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!
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.
(I have very briefly mentioned some stuff here: >>46586406 but I can expand and be a bit more detailed as needed.)