Sorry for being anecdotal, but I've often seen people buy something after failing to pirate it. But whether somebody has uploaded a font for illegal downloading or not should not be able change its fair market value IMHO.
In reality it does, and that is why the market's reaction may be just as unfair as up-front payments. (And I think your initial reply was related to fairness, correct me if I'm wrong.)
Indie music can always fall back on giving away tunes to support a touring and merchandising play, but someone that puts years into a font only to see it pirated isn't exactly given the opportunity to rent a tour bus.
I think that if he can make it work, he deserves our encouragement.