There's some great work going on there - the big difficulty isn't the producing or financing, though. I'm part of the Seattle webseries community, and the big difficulty I keep seeing is - how do you get your series in front of people?
So in a sense - I think marketing is the killer if you're going to compete head-to-head with Hollywood.
A simple answer would be 'social proof'. Mashable provides a TopTen list of the most watched shows. That's a good start but the site is too distracting for Average Joe, in my opinion.
Also, web series are too short for true passive entertainment. I guess what your communities would need is a sort of Google Adsense, so you could plug-in advertising to be able to produce longer streams.
That would at least provide you with some money. When one show hits it big, that'll make news, and more people would start looking for shows like that. More eyeballs, more advertising, better chances of another hit, more news, and there you go.
You don't need to out-market Hollywood (though achieving parity may be part of the equation). You need to create a more efficient production cycle, from artist to costumer.
I'm thinking lean start-up. How can we reduce cycle time between artist conception of an entertainment pitch and consumers evaluating it?
Lean Start-up says reducing this cycle time should make the system fitter.