It also helps if you can put up a mini site or some content and start driving some traffic. Selling a domain that already has traffic is always worth more than a domain with just a "cool name". Obviously there are some exceptions, but finding a name that is highly desired by someone else is no easy trick.
Yeah I don't think there's much money to be made here unless you get really lucky and all the good ones are already taken. I see plenty of people trying to sell their domains asking ridic prices and nobody ever buys them. There's so many domain extensions these days that you can always just purchase a different one any way.