Matthew Prince is definitely not a good actor, but that's not the point. What Cloudflare did was they acted like good people, said good things, even did some good things, but once they got enough business and momentum, they then started doing shadier and shadier things, and now they're a protection racket that is happy to protect scammers for a fee. I think Cloudflare's most ardent fans would have trouble articulating technically valid reasons for why it makes sense to re-centralize the Internet around them, yet that's exactly what Cloudflare want.

That's why people don't necessarily, and shouldn't, trust that Tailscale won't head down the same path. It's hard enough for non-profits - heck, the Mozilla Foundation is losing all the good will they've ever had, and even the Raspberry Pi Foundation decided to gaslight people when they started eyeing corporate money.

If there's an open source way to do a thing that's a pain in the ass and a way to do the same thing from a for-profit company, I'll take the pain in the ass thing every time. History has shown it to be the prudent thing time and time again.