Judging character & building trust

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AS men, educate me. I have watched the AS man in my life trust and accept the wrong women (crazy, abusive, drug addicts, gold diggers) and mistrust and reject the right women (clean living, professionals, open-minded) over and over. The bad ones predictably burn him, so he won't really give the good ones a chance. Why does he do this? He seems to seek out flawed women, perhaps expecting them to be more forgiving toward him, but that is never how it works out. It's almost as if he seeks to have his fear and mistrust confirmed. As if he prefers be right, and alone, than to take a chance on a healthy, loving relationship.

So is it more than just difficulty sizing up intentions? Is there an element of self-punishment to it? Self-doubt that he can do any better? Fear that he isn't worth any better? Please tell me about your thought process when you are judging a person's character. What makes you trust or not trust a person? What other "hidden" factors play a role?

To be honest, I distrust everyone but my family, closest friends, and people much older than me. Everyone my age seems to view backstabbing, dishonesty and gossip as a fine art.
Even people who seem open-minded and friendly art first can turn out to be awful people. It's not easy to trust people if the precedent is that they'll try talking to me a bit, seeming friendly, then suddenly start badmouthing other people I know and expecting me to join in on the gossip. Nearly everyone does that. As a result of that, I generally assume everyone I haven't known long enough to have bad intentions.
See, this is the reasoning - they're apparently willing to hurt others behind their backs, so they will do that to me, and it proves them to be two-bit cowards.

There are, admittedly, some people I'm willing to trust earlier, and some I'll never be willing to trust. It's easier to trust someone who is completely honest about their intentions. I'll never trust anyone who dresses like a rapper, and I usually won't trust anyone who is too much in line with the latest fashion. Usually, their way of speaking is equally telling - some people have a tone in their voice, and sometimes an accent, that reveals to me immediately, before I've even spoken to them, that they're worthless, dishonest people and that I should avoid them if I can.

It would be much better if everyone was just open about their intentions. What I see here, in all of mankind, is a prisoner's dilemma in which those who decide to be open and honest lose out. If, in a three-person conversation, one is honest, he'll be at a comparative disadvantage if the others are dishonest. And there's no good way of telling if someone is being honest, so it's best to not risk anything and simply be dishonest.