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.
There was a popular post less than a month ago about this recently >>46305585
I agree maintaining wireguard is a good compromise. It may not be "the way the internet was intended to work" but it lets you keep something which feels very close without relying on a 3rd party or exposing everything directly. On top of that, it's really not any more work than Tailscale to maintain.
It's worth an assessment of what you _think_ running ssh on a nonstandard port protects you against, and what it's actually doing. It won't stop anything other than the lightest and most casual script-based shotgun attacks, and it won't help you if someone is attempting to exploit an actual-for-real vuln in the ssh authentication or login process. And although I'm aware the plural of "anecdote" isn't "data," it sure as hell didn't reduce the volume of login attempts.
Public key-only auth + strict allowlists will do a lot more for your security posture. If you feel like ssh is using enough CPU rejecting bad login attempts to actually make you notice, stick it behind wireguard or set up port-knocking.
And sure, put it on a nonstandard port, if it makes you feel better. But it doesn't really do much, and anyone hitting your host up with censys.io or any other assessment tool will see your nonstandard ssh port instantly.
Now, I do agree a non-standard port is not a security tool, but it doesn't hurt running a random high-number port.
One less setup step in the runbook, one less thing to remember. But I agree, it doesn't hurt! It just doesn't really help, either.