This is your problem. You don't know what is or isnt in your own best interests. First you become vulnerable to a guy that lives two hours away from you and could very well tell you anything and you'd be unable to prove him right or wrong, then, without being in a committed relationship, you go ahead and have sex with him. If you have to play games to get him to pay you attention then He's Just Not That Into You. Read the book and learn what women like you do that backfires on them.
To top it all off, you're contemplating going out with someone who is hardly come to terms with the end of his relationship if he's still living with an ex. I'm beginning to think you're afraid of commitment and so you are drawn to people who are "safe" to you because they are unable to get too close to you because of their circumstances. Then, when the don't get close you do stupid shit to compensate.
To answer your question. NO don't go out with someone who is still living with their ex. If he had his shit together, he'd leave and get her a room mate that was willing to cover the other half of the rent. For all you know he's still very much still doing her and just feeding you a line of horse shit. Stop trusting people you don't even know. Trust is earned and no sense wasting your time on people who are'nt free of ex baggage yet. O.o
Even if you are a man posing as a woman, that still applies to you.