While I understand where Matt is coming from, i.e to stick with the spirit of open source, he also has to see that even though WordPress.org is free they do charge for some select options on WordPress.com and a heck of a lot more on their VIP service. I believe this helps them stick with the spirit, for that warm fuzzy feeling as well as a warm healthy meal.

It can be a challenge to go down that route though, as the majority of people will expect it for free.

Matt, you could have easily channeled your resources into one or two major plugins and offered upgrades for a fee. There are many people who appreciate extra features and support that way. We've been moderately successful with this (for the amount of time we spend on it) and I believe someone of your caliber can be as well.