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.
I am not sure why people are so afraid of exposing ports. I have dozens of ports open on my server including SMTP, IMAP(S), HTTP(S), various game servers and don't see a problem with that. I can't rule out a vulnerability somewhere but services are containerized and/or run as separate UNIX users. It's the way the Internet is meant to work.
Similar here, I only build & run services that I trust myself enough to run in a secure manner by themselves. I still have a VPN for some things, but everything is built to be secure on its own.
It's quite a few services on my list at this point and really don't want to have a break in one thing lead to a break in everything. It's always possible to leave a hole in one or two things by accident.
On the other side this also means I have a Postgres instance with TCP/5432 open to the internet - with no ill effects so far, and quite a bit of trust it'll remain that way, because I understand its security properties and config now.