20 something gigs? Really? If that was it I wouldn't spend the time with answering the question! I am talking about 350-400 events per year (15 DJs on staff). OF COURSE personality makes the difference, but in Washington DC metro area there are some clients that want personality, others that don't. Some want to pick out all the music, some none of it. We have backup equipment, experience, etc. and the $400 DJ always promises the same thing and doesn't deliver. The things you point out are true, but are only view AT the event. The cheesiest DJ in the world thinks (and says) they are not cheezy and have a great personality. Problem is - clients believe it.
Um, I think we're talking about two different kinds of personality. From what I gather (and please correct me if I'm wrong) you're viewing personality strictly in terms of over-the-top extroversion or "cheesiness". What I'm talking about is personality, in the psychological and sociological sense; what makes you different from everyone else. Figure out how to market that and you really won't have to worry about the $400 DJs, the gigantic multi-ops, or the 22 year old DJs doing it "as a great way to meet chics."