Zerotier has had all of that figured out for years, in the meantime Tailscale just locked the thread requesting multiple connection support as "too heated" (after >2 years of no progress).
And putting access to our corporate networks in the hands of Google & Co. and their trigger-happy account-blocking algos means that TS gets an automatic thumbs down from compliance officers at several of our clients. We can read stories on HN every week why such authentication systems are a bad idea, and steadfastly refusing to roll your own account system (all the while justifying it with handwavy security concerns) just seems lazy to me.
I can follow their arguments to some extent, I just don't understand why the TS people insist on exclusionary features rather than letting the user choose. You believe multiple simultaneous connections are somewhat insecure and that's why you won't implement it? Okay, slap a warning sign on it if you want, by all means, but who cares about this if all I want is to connect to 5 branch offices at the same time.
You believe forcing users to use their private, everyday Google or Github accounts for authentication is safer than using a special account registered on TS with safe, unique credentials not used for any other purpose to minimze collateral damage (if the Google or Github credentials get compromised you'd get their emails or a bit of source code, but not access to the WHOLE corporate network)? How about letting the user choose and show some flexibility to use-cases that exist even if you can't imagine them?
Sorry for the rant, again, I want to love TS, it's UX is pretty neat, but something about their supercilious attitude with which they justify their (non-)features just rubs me the wrong way, I guess.
At the risk of downvotes (because I know TS has - rightfully - many fans), if anyone from TS is reading this, I do implore you to be more open-minded and give your users a choice rather than patronising them on multiple fronts when using your product. Feel free to recommend a "best practice" but understand that many users who might love your product will want and have to use it in a slightly different way than you intended - and that should be okay.