Tailscale is just an added unnecessary external dependency layer (& security attack surface) on top of vanilla Wireguard. And in 2025 it's easier to run vanilla Wireguard than it's ever been.
The selling point of Tailscale is that they simplify Wireguard UX by adding a proprietary control server - this adds complexity to the stack (extra component) but simplifies user experience (Tailscale run the control server for you).
Headscale seems like it's complicating the stack (adding an extra component) as well as complicating the user experience (you have to maintain two components yourself now instead of just the one Wireguard instance).
Granted I presume the Headscale control server might simplify management of your Wireguard instance but... you're still maintaining the control server yourself.