I want to make a few things clear, first of all UPenn is not a backup nor my "safety" school. UPenn is a great school otherwise it would not have ended up on my list. I am very excited about the oppurtinity to pursue my PhD at UPenn. I really like the research there and the point of this thread is to explore whether I am getting a bit too greedy or whether I actually have a chance at my top choices. From the amazing advice and responses I received I would guess that reapplying without significantly improving my application (i.e. investing a year or more in to profound research at some institution) would not actually get me in to my top choices as I have been rejected twice.
With that said, I am definitely going for UPenn. Are there any others who did not get in to their dream schools and still doing great at their current university?
Thanks again for the amazing advice and insight. Also thank you all for being open minded about a question that is emotionally, rather than, rationally driven.