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.
In my experience this is much less of an issue depending on your configuration and what you actually expose to the public internet.
Os-side, as long as you pick a good server os (for me that’s rocky linux) you can safely update once every six months.
Applications-wise, i try and expose as little as possible to the public internet and everything exposed is running in an unprivileged podman container. Random test stuff is only exposed within the vpn.
Also tailscale is not even a hard requirement: i rub openvpn and that works as well, on my iphone too.
The truly differentiating factor is methodological, not technological.