Ok, it is possible to achieve your goals. I am not trying to be a motivational speaker, but if you really work at it, you could end up where you want to be. Here is the most important things to keep in mind. 1) With your current GPA, you will need to do well on the sat/act test applicable to your state in order to attend either morehouse or alabama, and keep that GPA up or even a bit higher ending out your senior year.
2) The 2 years you are in your first school, you will REALLY have to prove yourself through grades and achievement. Im talking insane high standards if you plan on transferring to a ivy league school.
3) Don't get sidetracked too long at the insurance gig, because schools look negatively on too much time in a transfer, and you don't want to lose focus.
4) If you manage to get into the ivy league school, you gotta keep those high grades, which doesnt mean all brains, most of it is hard work. AND you will want to do whatever you can to pull off an internship or two (even unpaid) in the private equity to get your foot in the door.
Just remember, its all about hardwork, and secondly, I know its your dream, but you dont have to prove anything to anyone. Richness and success are not necessary to be happy, but you can achieve them if its your goal.