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.
TS is cool if you have a well-defined security boundary. This is you / your company / your family, they should have access. That is the rest of the world, they should not.
My use case is different. I do occasionally want to share access to otherwise personal machines around. Tailscale machine sharing sort of does what I want, but it's really inconvenient to use. I wish there was something like a Google Docs flow, where any Tailscale user could attempt to dial into my machine, but they were only allowed to do so after my approval.
For the permissions, just add basic auth in the reverse proxy and choose whom to share the passwd with.
Now if you want OAuth or something like that... well tough luck, you need to set up OIDC or whatever and that's going to be taking you some time, but it still works how you want.