The moment the inevitable enshitification will start at Tailscale, this feature will go away.
I’m saying this as a currently super happy Tailscale customer who was burned multiple times in the past by other companies being sold or running out of VC money
That feels right to me. Headscale is mostly used by home labbers and small hobby users, it competes with self-hosted OpenVPN and WireGuard, not Pulsesecure, Cisco Anyconnect or GlobalProtect. It's a way to introduce Tailscale to people who love to try new shiny tech in their spare time, but don't want to give up control over their infrastructure.
Those people will then bring their Tailscale expertise and enthusiasm to work. Work really doesn't like managing IT infrastructure unless it's one of their core competencies.
Sure, some companies will actually choose Headscale over Tailscale proper, but I suspect that's a small minority (especially if you take company size and the money involved into account). That's just cost of revenue, not unlike Facebook advertising or billboards on the side of a road in Silicon Valley.
I have the same memory. But they may not feel that way forever. Many a company started by attracting developers with a generous free tier or open-source offering, then started to clamp down once the going got tough.
Heck, it happened to one of Tailscale's competitors, ZeroTier, which used to release their client software under GPLv3 but eventually switched to BSL.