> What Tailscale doesn't solve is access to the data that web app serves if the user's machine is compromised, as tailscale is just determining "can the user hit the webserver on port 443?" and does nothing to evaluate the state of the user's host.

Tailscale has some cybersecurity integrations to configure access depending on the device posture. For example, blocking access to a webserver if the device is out of date, or if malware is detected, or if the firewall is disabled, etc. But I don't use any of those integrations and can't speak to them.