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Physics
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From experience do not apply to your top school first unless you've worked on it extensively. My top school was Wharton and my app was a hot mess. But my essays got better after every school to the point where I applied to Chicago Booth R3 and was accepted. The sweet spot is to apply to your top school 3-4th. This way you can apply lessons from previous applications but you aren't burnt out.
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I wanted to get it all done and couldn't have imagined splitting it into two rounds. My suggestion is to apply to 3-4 schools in the first round and have 2-3 schools for round 2. One or two should be "back-ups" in case you don't get in anywhere in the first round, and one should be a school that you'd take OVER the ones from the first round. I didn't do it that way, but it sounds like you are having trouble ranking them. Since Columbia is rolling, the earlier the better, but just be sure to get it in by the scholarship deadline if finances at all matter to you.
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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.)
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Your order would be possible, the only snag is that you will need to submit a deposit to a school to hold your spot. Only in rare circumstances will they allow you to hold off making a decision, and even then, it's usually only for a week or so. Basically, you're out of between $2000 and $3000 if you do it that way.

I agree that you are starting early - though indeed, it's never too early! - so you may be underestimating yourself. I applied to all 4 of my schools in one round and am quite grateful I did. Applications get better with time, but there's also burn out to keep in mind. If you put together drafts now, you still have plenty of time to let them sit and revisit them with fresh eyes.
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3hrMBAapp
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I agree with the thought process that you should apply to first choice schools first.

In my experience this year, and it varies with schools, is that the deposit deadline is sometimes negotiable.