I’ve read a lot of recommendations for tailscale and am on my way to try it out myself. Do you use Tailscale in the “normal” way or do you host your own Headscale server (as I’m planning to do)? Any pros and cons?
I started using my own WireGuard config instead of using tail scale. Works great for me, though it does take more work up front.
I started out with WireGuard. As you said its a little finicky to get the config to work but after that it was great.
As long as it was just my devices this was fine and simple but as soon as you expand this service to family members or friends (including not-so-technical people) it gets too annoying to manually deal with the configs.
And that’s where Tailscale / Headscale comes in to save the day because now your workload as the admin is reduced to pointing their apps to the right server and having them enter their username and password.