I greatly appreciate the feedback. A lot to think about here.
I don't think I was entirely clear in my opening post. Due to timing, I will at best (though maybe unlikely) be able to apply to 3 schools in the first round. Columbia is rolling I'm aware, but as machichi mentioned, there is a scholarship deadline. Let me put forward a hypothetical: Let us say that I think that Wharton, Columbia, and Booth are all stellar schools and I have them weighted equally. During round 1 I apply to Wharton, Columbia, and Yale. Columbia dings me, but Wharton accepts me. At this point, can I still apply to Booth in round 2 and then wait to hear back from Booth after round 2 to make my decision? Or will Wharton expect an answer and my offer will expire prior to me obtaining a result from Booth?
I apologize if I am missing something obvious.
In regards to when you should apply to your "dream schools", I am torn on this issue. I will need to make that decision soon!
(by the way Timbob you made my day by telling me I am starting early. I am just beginning and feeling tremendously behind.)