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!
I enjoy that relative "normies" can depend on it/integrate it without me having to go through annoying bits. I like that it "just works" without requiring loads of annoying networking.
For example, my aging mother just got a replacement computer and I am able to make it easy to access and remotely administer by just putting Tailscale on it, and have that work seamlessly with my other devices and connections. If one day I want to fully self-host, then I can run Headscale.