[floundy]

So the way I understand Tailscale is that it's built on top of Wireguard; Tailscale claims it's "easier to use" but I haven't found Wireguard to be difficult to configure at all. Are there any extra benefits to using Tailscale that I'm overlooking?

[MattTheRealOne]

Yes, Tailscale uses Wireguard. If you can use Wireguard, that is great. That is not an option for many people who are behind a CGNAT and/or do not have the ability to setup port forwarding. Tailscale also makes it easier for sharing access with other users.