I’ve really wanted to try tailscale. I fear I’ll like it, and I don’t want another company to have a monopoly on simple things so everyone forgets how to do them.
My escape hatch from the monopoly is headscale[0] which I can self host.
More to the point, I hope their technology becomes commonplace & gratis a la LetsEncrypt for SSL Certificates.
Look at email. It’s basically a “lost technology” in that it is nearly impossible to self-host (though there are people out there doing it, there are very few modern guides from zero to production). Same with file sharing and IRC servers.
Maybe I’m just rambling in my “old” age…
However, when you have 10 nodes and need to add one more node, you now need to update all other nodes so they can speak p2p. Management with scale is the struggle.
Furthermore you could extend this argument almost every other cloud service with a primary feature of "convenience" and/or "management". Just build everything yourself.
If this means I continue to forget how to run OpenVPN I consider that well worth it.