I wouldn't and the MAIN reason is that I don't want her family become a liability to me. Trust me I have seen first hand, and it breaks families.
I had a conversation with a friend last week about this subject and he told me I was too picky. He even said that he would marry a waitress; I told him I wouldn't and he looked at me as if I was crazy. I want to marry a woman who is independent and who would be more of an asset than liability. Now I'm not saying I want a Paris Hilton but I would prefer my wife at least be from a upper middle class background. There are pros and cons to marrying chicks from humble backgrounds but the cons outweigh the pros for me. When a lot of humble chicks get a taste for money, they become greedier than even some rich chicks. This is due to the fact that they grew up with nothing and now feel that they are deserve the money since they grew up poor (like most celebrity divorces when a rich man marries a poor woman, she leaves with half and starts flossing with the guy's money like she's the baddest bitch).
I know I'm going to get shit thrown at me for this but I feel that this is a legit topic especially since most of us on this board have aspirations to become Big Swinging Dicks someday. With that said, let's discuss.