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.
I'm in the middle of setting up my own homeserver. Still deciding on what/if I want to expose to the internet and not just local network and while setting everything up and tinkering is part of the fun for me. I get some people just want results that they can rely on. Tailscale, while not a perfect option, is still an option and if they're fine with the risk profile I can understand sacrificing some security for it.