1) If he comes from a family that is not frum, what do you think he does for shabbos? How could he NOT have a close relationship with another family? Similarly, it's very unusual for children of divorced parents NOT to go through therapy.
Also, you still should not call someone like this a "divorced boy". It does not define him. It's like when people refer to me as an "orphan" because my father passed away. It's very hurtful, not to mention inaccurate. There are so many aspects to this boy's personality and you keep fixating on the one thing that he actually can't control.
2) You didn't actually answer this.
3) It doesn't matter how "reasonable" your parents are. At some point everybody needs to acknowledge that you are an adult. Think of it this way-- do your parents currently have veto power over anything else in your life? Will they have veto power over anything once you are married? If not, why should this be any different? Of course you should take their advice very seriously. But they need to respect your judgment, and when there is disagreement they need to trust you. We're talking about one date here. It's not like you're getting engaged to someone they don't like.
4) The "upper hand"? Really??
"strong family" See #2.
"stronger yiddishkeit" How do you know? Many baalei teshuva actually have stronger yiddishkeit because it's something they chose.
"stronger desire to support someone in kollel" This actually makes no sense...
"stronger finances" This is a problem? Many, many families are structured this way nowadays.
Whomever you marry, he will be stronger than you in some areas and you will be stronger than him in some areas. Hopefully you will balance each other out well. There is no boy out there, no matter how pathetic you may think he is, who is not stronger than you in something. Likewise the opposite. But the important thing is that you have a committed and respectful relationship. It's not a contest. My father was a baal teshuvah and my mother, who is FFB, helped him learn Hebrew. One of her friends said to her, "I don't know, [my mother's name], I think the guy is supposed to know more than the girl..." Who says? Why does that have to be the case? He was stronger than her in other areas and it worked great.