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!
Why did people use Dropbox instead of setting up their own FTP servers? Because it was easier.
Being a software engineer doesn't mean you want to spend you free time tinkering about your self-hosting setup and doing support for your users.
With Tailscale, not only you don't have to care about most things since _it just works_, but also on-boarding of casual users is straightforward.
Same goes for Plex. I want to watch movies/shows, I don't want to spend time tinkering with my setup. And Plex provides exactly that. Ditto for my family/friends that can access my library with the same simple experience as Netflix or whatever.
Meanwhile, I have a coworker who want to own/manage everything. So they don't want to use Tailscale and they dropped Plex when they forced to use the third-party login system. Now they watch less than a third than they used to be, and they share their setup with nobody since it's too complicated to do.
To each their own, but my goal is to enjoy my setup and share it with others. Tailscale and Plex give me that.
Choosing convenience is fine. But if basic port forwarding or WireGuard is beyond someone's skill set, "software engineer" is doing a lot of heavy lifting.
I am not saying they are, but if it really is the case, then yeah.
As for file sharing... I remember when non-SWEs knew how to torrent movies, used DC++ and so on. These days even SWEs have no idea how to do it. It is mind-boggling.