Tailscale is slloowwww and I'm not a big fan of someone else controlling my network. Yeah, tailnet lock at all that, I know, but still...
Two cases I can think of are MTU misconfigurations and constrained CPU on either endpoint, where the node CPU can handle non-VPN network demands but can't handle the VPN demand.
I set it up, and it worked, but regular Tailscale works so well out-of-the-box that I just used that instead of maintaining headscale.