I've got a friend who has been doing it for a long time, blasting it with out source workers. He's got the operation, but by what I've picked up off his vibe is that it's getting tougher.
Craiglist is evolving to fight, flag, and ghost CL pros. Overall I think it's a wash as those who have the advantage of keeping up lockstep with CL will gain greater share as more newbies attempting to game the system find it impossible.
$ itself isn't the issue, it's just 1 variable in the ROI. The operation counts for everything as the sell just needs to be a bit more at a premium.
Personally I think it would have been cool to get that system made, but I'm not inspired in that direction because I think it's oversaturated and that there are easier ways to make money.
Best of luck air360, if I were you I'd hit up some freelancing sites the old fashion way looking for those who are up to speed on CL tactics. I totally agree that pool is drying up fast :/