Honestly, anixi, I think you are reading way too much into it. For one thing few if any bike flippers are going to be incorporated. And while there are doubtless some people in a large market like Chicago making some part of their living from flipping bikes, including flogging their ads on CL over and over again, it is clearly not much of a living.

I think people just get annoyed at the ads, for reasons that are reasonable or unreasonable, depending on your viewpoint. Sometimes it's because of an actual violation of CL ads, like posting the same ad day after day or even multiple times in a day. Sometimes it's a self-appointed CL policeman 'protecting' the public from misrepresentation, and as we've seen some posters here feel they should provide that role. But that can easily go off the rails as sometimes the 'protector' simply doesn't understand what the seller is offering, like with Robtown's bike, or it's just a disagreement about value, in which case the market should decide.

Yes, there are a few people who don't think I should be able to buy a bike at a yard sale for $5 and sell it the next day for $100. But I think self-appointed experts are much more the problem.