Realistically if you can work on a small and high profile project like tailwind you're gonna be snatched up by someone willing to pay you at or near FAANG levels

That's good. We can tell people that so they will submit us patches for free.

Maybe we could even have a neat website with a leaderboard of sorts where we honor top contributors like some kind of gamification.

I think we would really need about five highly opinionated people with good technical and people skills to volunteer as paid maintainers for tailwind or any oss project to succeed.