PyCon seems to be some sort of an amazing global annual movement. I haven't gone to one yet (I do have a plan in the future to do that) but I know that many more countries want to have a local PyCon as well (to cut the transportation cost). They have the people but lack of the Python skill, marketing, and organization.
I think in about 5 years or so we will see more and bigger local PyCons.
The PSF helps out local conferences as much as it can - any "revenue" from PyCon is sent back out by the board of directors to local conferences in many, many countries. Check out http://pyfound.blogspot.com/
Yeah, I noticed that PSF is trying to support local communities as much as they can as I did their recent survey for the local communities. The survey questionnaires are focused toward "How can PSF help you to grow your community".
I think in about 5 years or so we will see more and bigger local PyCons.