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.
You have also added attack surface: Tailscale client, coordination plane, DERP relays. If your threat model includes "OpenSSH might have an RCE" then "Tailscale might have an RCE" belongs there too.
WireGuard gives you the same "no exposed ports except VPN" model without the third-party dependency.
The tradeoff is convenience, not security.
BTW, why are people acting like accessing a server from a phone is a 2025 innovation?
SSH clients on Android/iOS have existed for 15 years. Termux, Prompt, Blink, JuiceSSH, pick one. Port N, key auth, done. You can run Mosh if you want session persistence across network changes. The "unlock" here is NAT traversal with a nice UI, not a new capability.