re: 4+ You Forgot Pterosaurs
Good point re pterosaurids, so four times. Ants did evolve from wasps (and have the ability to fly, anyway). I'm pretty certain all flying insects have a single flying insect ancestor.
There was a South American bird that was in pterosaurid-size category.
I think the point remains that for hundreds of millions of years, there was only one jump to powered flight (even if later multiple species radiated from that original flyer), and a scientist might make the same mistake about flight that I think we're likely making about tech civilizations.