1. Operating Systems take a long time to develop. The process can take years.
2. Operating Systems have a value. If they didn't people would be content just using punch cards.
3. People that do this work should be compensated.
4. Trying to figure out a solution to this problem, both from a customers and creators view is more beneficial than the "fuck this, fuck that" rhetoric among linux nerds.
I apologize for the snark. My point is that there's a striking similarity here. There are some arguments that Windows is superior to Linux, and once upon a time, those arguments might've been valid. They're not any more. It's crazy these days to plunk down $300 for Vista when Ubuntu is better, and free in every way.
Quantity leads to quality—even if the average free font is much worse than the average proprietary font, a few of them will be very good, and will gain a lot of usage.
There may still be a place for proprietary fonts. But the web will embrace the more open option. If the foundries want a piece of that action, they're going to have to change the way they do things.