I noticed today that MyFonts' search accepts the "*" regular expression, http://www.myfonts.com/search/*/fonts/
This offers a view at the size of the type design community. Obviously not every family and foundry is on MyFonts, but I think this offers good ball parks:
* 31,164 32,000 font families
* 23,383 24,000 font families available as web fonts
* 3,892 4,000 individual type designers
* 1,915 2000 professional font foundries
Does this sounds about right?
Also, I seem to recall that MyFonts used to list font files, not font families, but I can no longer manage to see that kind of information.... I see "55,000 fonts" mentioned across the web, but I wonder how many font files have actually been released... Any other (better?) ways to gauge that, and such things?

* I offer the current exact numbers returned on the search page, struck out