Unique Essays

I feel like my essays will get me into B-school because I am a good writer and have good stories to tell, but I'm not sure what is better left unsaid. For example, I grew up in a single parent family (my father died when I was 9), but nonetheless it was still a middle-to upper middle class town and a great school system.
I am only the third to graduate college in the family- after my father and 3rd cousin and will be the first to pursue graduate school.
My greatest accomplishment to date is getting into my undergrad institution- top 30 (it was top 25 when I was there) and I was initially waitlisted (guess they had enough people from NJ...what else is new). It was my dream school and I wouldn't let it go so I wrote an award winning play because I knew it was an extra letter my guidance counselor could send to the school to push me over the edge. It worked.
My career life has been quite similar- took a Wall Street job in a highly quantitative area. When my quant skills came into question I passed an extremely intensely quantitative test which has a 42% passage rate (not to mention it felt like I was the only non-middle-aged man in the room).

I think these things show that I work hard to achieve my passions, whatever they are at the time. Not to mention I self-financed my education and am still paying the loans.

Finally, I don't know if this is anything to write about at all but my brother has been convicted of a couple of different crimes and it has been a huge family issue dealing with it all (my mother took a 2nd mortgage to pay for lawyers, etc.) I don't want to write an essay conveying my family is white trash or using my brother's bad situation to my advantage or anything like that because that is so not true, but is this something that I should write about in terms of obstacles I've overcome? Or is it better left unsaid? I am completely embarassed by this situation and the fact that he is 30 and living at home, and I would hate for an interviewer to pry further into the convictions because I can't bring myself to talk about them. What do you guys think?