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In 1992/1993, I applied to 5. I applied to UVA, Michigan, William and Mary, Wesleyan, and Penn. I had an application to Howard, but had no intention of going there (sister was a student there, and it was 2 miles from home); I sat on it until the last minute, and I got accepted somewhere else and put it in the trash.
My (expensive private) high school had an incredible college advising team with these very elaborate relationships with colleges, so I had very skilled people helping me target a reasonable number of schools, choose a safety school, choose a reach school, find schools where I was very likely to get in, etc. There were very few surprises in the results.
The results: Wait listed but didn't pursue it at Wesleyan. Got a letter from Penn telling me they couldn't find my application check, and then a rejection letter a day later (I probably got rejected for being too dumb to staple the check to the form, which, fair enough). Got into W&M but it was too far from civilization; I never even visited.
It came down to UVA and UM and I picked UM, which probably was my first choice all along.
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