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.
This is what I do. You can do Tailscale like access using things like Pangolin[0].
You can also use a bastion host, or block all ports and set up Tor or i2p, and then anyone that even wants to talk to your server will need to know cryptographic keys to route traffic to it at all, on top of your SSH/WG/etc keys.
> 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.
This is what I don't do. Anything that needs real internet access like mail, raw web access, etc gets its own VPS where an attack will stay isolated, which is important as more self-hosted services are implemented using things like React and Next[1].
[0] https://github.com/fosrl/pangolin
[1] >>46136026
I personally wouldn't trust a machine if a container was exploited on it, you don't know if there were any successful container escapes, kernel exploits, etc. Even if they escaped with user permissions, that can fill your box with boobytraps if they have container-granted capabilities.
I'd just prefer to nuke the VPS entirely and start over than worry if the server and the rest of my services are okay.
there are some well respected compute providers as well which you can use and for very low amount, you can sort of offload this worry to someone else.
That being said, VM themselves are good enough security box too. I consider running VM's even on your home server with public facing strategies usually allowable