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But if you are socially ranked way lower than a woman (e.g. you are a college dropout with a regular job, she has a masters degree in biz and a rocketing career, making lets say $ 20,000+ / month) the game is different. You will have a very hard time DHV'ing yourself career-wise, one thought would be playing the badboy card, we all know the nice and successful women love the badboy!

You should never DHV on things you are weak in. I would almost advise against the bad boy card because there are bad boys at all social levels, so you just be blending in with the rest of the bad boys out there. I think presenting your self as something that is out of the ordinary and intriguing would do better.
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Otherwise.. She is probably very result orientated, so if you don't have any results to back you up, you'll need a good story to explain her, why you haven't really had a breaktrough in your life.
I say this is age dependent. If your a 25 year old guy, I don't think she would expect major things from you but more a path and a goal. Now if your a 35 something guy then you would need the story.
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I know many high class women and having dropped out from college (or something similar) is a major turnoff and DLV for them.
I would say overall this is true. Unless your someone like Bill Gates and is going somewhere.