I was thinking about this and got a bit of an idea on how to raise money without driving people away from the site.
Ever heard of a "swear jar"? It's a jar you put money into each time you swear. Put a system like that in place, but instead of a swear jar you give money to the site, and instead of swearing you buy the right to break a rule on the site that would normally result in an infraction. So for example, if I gave $5, I could use the F word and tell MobBoss to F off or something and for $10 I could post some tits in the babe thread and let's say $1 to respond to a moderator comment in public sarcastically. I don't see how you could go wrong with a system like that!