What you are decribing may have nothing to do with DMOZ. Your friend with the crappy site, is it a poker site? Does he go out to play poker in casinos and chat up everyone at the table, and pass out business cards with his site on them? You can drive a LOT of business personally if you go to places that have your target audience and sell. I know a poker teacher that makes good money just sending students through their site.
I know exactly what you mean but still, there are many sites out there that get more than 1-2 visitors a day without going out and do landbased advertising. This type of advertisment as well as going door to door with casino CDs would be my last resort if there is no hope for online success, the problem is there isn’t many casinos if any that are close to where I live. My friend also doesn’t go to real casinos either as far as I know, he owns just a plain crappy casino site with about 10 pages with just one or two casinos and thats it with no poker at all on it the last time I saw it.