I have very rarely been successful by booking a place cheap. I did this some before I figured it out. You book a job for $50., then that is your price. Can't say as I've ever booked a job at half price, or auditioned for free and got hired at a higher price. Maybe I'm not good enough, but it just usually doesn't happen, at least in night clubs.
I'm glad I've been lucky enough to have reached a point where I don't have to go out and hustle jobs, because that's the part I've always hated the worst.
As a matter of fact, a few years ago, I just arbitrarily doubled my price for private parties (at least for first-time clients), thinking I probably would get a lot fewer, but come out about the same. Wrong, if anything my number of private parties increased. Perceived value maybe? I don't know, but it sure had a positive effect rather than what I expected. Maybe I wasn't charging enough in the first place? . . . It helps that I get a lot of exposure to more affluent clientele in the venue where I perform regularly.