Aw, damn, I had a long, bitter, and surprisingly cathartic post about a con we ran that went pretty badly, but then I hit the wrong button and lost it. Grrrr.
But, anyway, it boils down to this: Everybody in our gaming club thought we should run a small con. Everybody also mysteriously expected that the con would happen because somebody else would be doing all the work. So we had a serious lack of manpower, serious problems with people making comittments and then flaking out, and then “conversations” that nearly came to blows when people who had point blank refused to do even the slightest thing to help showed up a the con and said, “Wow. This is really lame.”
Gee, thanks, for pointing that out Sherlock. And what game are you running? Oh, yeah, that’s right . . . when we begged on our knees in every meeting for two months straight for people to run something . . . anything, a D&D module, a game of Settlers of Catan, anything you were all like, “I have too much homework! Waaaaah! Pity me! Waaaaaah! My major is sooooo much harder than yours! Waaaaaaah! I don’t have time to run anything, because my life is so terribly busy! Waaaaah!” Well guess what, Brainiac, when nobody can be bothered to run games, there will be no games run at the con!
pant pant pant pant
Not that I’m still bitter 5 years later, or anything.
Er, so anyway, we’ve been doing much smaller 2-slot “Gaming Saturdays” that are better suited to the pitiful level of commitment we can get from club members. We have some CCG tournaments that draw in some people from out of town, the FLGS shows up with CCGs and a few other things to hawk, there is free pizza in great abundance, and all in all everybody’s happy.
So, yeah, it all comes down to the people you have working with you. Start small; don’t bite off more than you can chew, and spend at least 20 minutes a day in soothing silent meditation so you don’t end up killing anyone. 
And FWIW, the con-artistry angle didn’t even occur to me when I read the title, but then I am a huge geek.