As far as the premium content idea goes, I think that Earwolf could dip a toe into these waters fairly painlessly and without committing yourselves permanently to the strategy.
I don't know if there are issues with doing this, but given that Scott Aukerman hosts Comedy Bang Bang -- I'm talking here about the live UCB show, not the podcast -- it would be (relatively) easy to sell audio (maybe even video) recordings of the live shows. If you follow the Doug Benson model of charging $1.99 for 90 minutes worth, and breaking down longer shows into 2 downloads at that price, it seems like there is real money to be made here. I wouldn't be surprised if Earwolf pulled down $50,000 per show after paying performers their royalties and the UCB a cut.
Of course, this is conjecture: I imagine that you have discussed it amongst yourselves and perhaps you've decided that you wouldn't make that much money. But I really think that you could easily get 50,000 paid downloads for CBB @ UCB. If you could convince Paul F. Tompkins to come into the tent, I would think the same of recordings of his show at Largo (rights issues for the songs would have to be ironed out, certainly).
Incidentally, I just donated $100 after Caroline replied to a comment I made at avclub.com. So when you're filthy rich, don't act too annoyed when I come to your palatial estate and ask to hang out by the pool.
