Using Tailscale is like using Dropbox back when it was new: it's "just X but without the setup or maintenance", which shouldn't be so gosh darn satisfying to use, but by jove, it is. It makes you feel less shackled by the constraints that defined your world before. Awesome.
I realise this possibly isn't going to make me look any better than everyone else here to you, but have you actually tried Tailscale?
It does seem to be a near perfect solution for a few very specific problems, with almost no downsides and a user interface easy enough that you could do it without any knowledge of the underlying technologies
Sure. I don't think tailscale does anything that's impossible through other means (cue comments about how anyone can recreate Dropbox with an FTP server, svn, and a fuse file system). IMO whats great about it is that it's easy to set up and is incredibly low maintenance (at least they way I use it).
Tailscale gives me some irrational sense of happiness because it *just works* and lets you do cool things like this without having to worry (too much) about security.
reply