They probably would dislike each other. In fact, I kind of see their relationship as a parallel to Mal's relationship with Simon. Where Simon's self sacrificial love is relegated to River, Mal's is for his crew and his boat, and they come to respect that in each other. It takes a while but they get that because it's something only they can really understand. And since I see Dean as being very similar to Mal in many respects - shoot first, ask questions later; falling for someone they can't really have; loving something or someone almost too much; being kind of an old fashioned gentleman - you worked that in really well.

That's exactly it, that while they have this rebellious thing going on, they know what's important and in fact have a stronger moral compass than those who sit back and let things happen.

Wow. Even your subconscious is awesome.

That's what's so heartbreaking about him; he compares himself to Sam and finds himself lacking but when he compares himself to his father, it's exactly the same. He's in this middle ground between the two and he sees that as a failing on his part, an indication of uselessness.