This is a bit wordy. Sorry.
Age 16: Prestige and Random Teenage Whims
The first time I applied to college, as a 16 year old (early graduation), I applied to MIT (because my dad went there and I liked building robots), Harvard (because they have a co-op program with MIT, next best thing was my thought), two northeastern liberal arts colleges (no good reason at all, my best friend was applying, never visited either), and my state university located in Hometown (safety).
Got in to only Harvard and state university. Went to Harvard because of name brand and incredible financial aid/scholarship but was incredibly unhappy there as a 16 year old and mostly just smoked a lot of pot and slept with every queer woman on campus in between freshman classes, moved back to hometown after one semester, went straight home, worked retail and took part-time classes at the state university in hometown.
Age 21: Money and Flexibility
Reset after 5 years (21 years old) and I had moved halfway across the country, toured with bands, lived in a few trees, founded a nonprofit, trained as a vegetarian chef, been a stripper, and done two terms in Americorps (back then they gave you $4,750 of scholarship money for each term you served). I realized it was time to get my act together, so I took classes at community college to prove I was still a capable student.
Then I applied to schools based on their ability to shape my own curriculum, alumni network, community service opportunities, ability to do original research, willingness to work with non-traditional students, and their student culture.
I ended up applying to Marlboro (Vermont) and Evergreen State (WA). Got into both. While Marlboro had a sticker price that was ~45K higher than evergreen, it turned out that after scholarships, both cost about the same. Decided on Marlboro.
Age 23: Location, Academic Rigor, and Financial Aid
After 1.5 years of deferring starting Marlboro every semester, admitted to self I was not moving to Vermont, applied to two local liberal arts colleges (Lewis & Clark and Reed) and went to Reed for the academic rigor.
Don't regret Reed for a second. I got full financial aid because I was a poor adult (~$11,000 income) didn't have to take out any loans, got my ass kicked academically and emerged out the other side smarter, and have gotten nearly all my jobs since graduating through the phenomenal alumni network. My only regret is they weren't very good at handling non-traditional students and the campus isn't set up for commuters or having a life outside school.