As I mentioned at TypeCon this summer, I think web fonts are different creatures than desktop fonts (just as desktop fonts are different creatures from woodcut fonts). The Web is a different medium than print - as such some fonts work better with the medium than others.
I wrote up a first pass at the broad characteristics of a font that make it work well on the Web, what I'm calling: 'web native' -
Web Fonts – Identifying a New Species.
I've boiled it down to openness and speed-of-communication in both letterforms (large x-heights, open counters, etc) and licensing (OFL, MIT, etc).
What have I missed?