One of my buddies a few years back was banking ~100k/mo profit with Chatroulette bots who told guys jerking off to "find me on adultfriendfinder!" That was all in affiliate revenue.

At some point you have to wonder when it moves from ethically wrong, to you're an idiot if you don't do it.

Well if the guys were willing to pay and adult friend finder were willing to give him the affiliate fees then I really can't see that it is morally wrong. I can see it being pretty awesome.

I have targeted some very specific jobs which are usually known as "sexy". I am not proud of it because I don't think it's very ethic, I can't imagine putting this on my resume and technically the challenge is nonexistent (a simple html page with some css, few hours of marketing) Though the service is real and people don't pay for nothing, at least it's legal...

What's unethical about this?

Okay ethic is not the right word. I just think that these are just 3 more website in the p0rn/dating/drugs Internet landscape, and technically very easy to do. I don't regret it, it's free money and other friends have tried the dating/porn market. One of mine was making 30k/mo via porn ads, another never made any money. It's just that I would now prefer to come up with a project which I am proud of, which can be of any help to someone, that I could talk about without wondering if the person in front of me thinks it's creepy... Soon soon :)

I'd imagine it's more about the stigma behind these dating sites. Fake profiles etc.