Tailscale... is not that good. The underlying wireguard is robust, but tailscale control plane is completely proprietary, as well as their DERP servers that it too often uses completely needlessly. They can also block you off from downloading it, updating, or logging in, if you happen to be in a wrong country.
I'm myself looking for an alternative to it, but having trouble finding something I could share with non tech savvy friends while not being as complex on my end as, say, open/strongswan ais. Any suggestions welcome.
Yep. That's the number one contender. Well right after overriding default DERP's with my own VPS machines. I'll definitely try it out over some weekend.
One of my other concerns with this and other solutions suggested is the reliance on wireguard which can be subject to fingerprinting and censorship. Do you happen to know if it'd be possible to swap out Headscale's implementation of wireguard to amnezia? I'll have to do my homework anyway, but who knows, maybe there are some pitfalls to avoid.