Should I go out with him and give him a shot?

I have been friends with him for a little over a year, and I know he likes me a lot. He's very hesitant because he doesn't know how I feel and so sometimes random things come out of his mouth like "if you had a clone, I'd marry her" or "you're the perfect mix of brains, beauty, and athleticism" and he's away for a few weeks right now--he said "don't get date some weirdo while I'm gone!" and jokes about things like that in an odd way. It's just that he's very prideful sometimes, he once said "I hate poor people" which, I was just like WHAT? We're in college hahah I'm poor...(I continued to be shocked at that comment, and still am) but he treats everyone nicely so I'm sure he didn't actually mean that. With his friends he can get arrogant. He has a big heart, is very ridiculously attractive, but also flirts with a lot of girls and seems like a player. I'm also a little worried he's just interested in me because I haven't shown interest in him. He wrote me this letter... two and a half pages long, hand written, incredibly thoughtful, and it says "miss and love you" at the end. I don't want to hurt him, and I do like him but I just don't know if I could be in a relationship with him especially because my brother hates him and I'm not sure my family will be very fond of him either. I feel like it would just be a lot of chaos. Then again, I guess I have no idea what he's like in relationships. We would hang out and play video games all the time, and I miss him. Not sure how to decide if I should give him the green light or just stay friends. We're both 21. I mean, he said he hates poor people and it's really hard for me to get over that. Am I judging him too harshly?
Should I go out with him and give him a shot?
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