I think a problem that bugs me a lot is how I see lots of people wanting to do lots of cool things, but they lack the appropriate guidance. We do that on a day-to-day basis, but what about the other folks out there who don't know about this place?
Usually forums, IRC, blogs help in getting immersed with anything, but I have a feeling that a startup with the primary purpose of "Enlightening" its users has yet to come.
edit: Basically what I'm shooting for is: how to get rid of the crappy forums and allow a truly easy and fun way to go about learning new things.
People go to college to learn about how things should be, but not how they are. Waste of time and money, sometimes.