Which cities did I expect to enjoy visiting, and which ones did I enjoy in reality? Here’s a 111%, completely, utterly, totally subjective look at 57 cities in North America, reduced to a scatterplot. Since the data labels might overlap, a link to the full spreadsheet is here.
Overall, I found that about 75% of cities are about as hyped as they deserve, with the hype being informed mostly by overall population and media buzz. This makes the outliers all the more interesting. The most overrated cities:
- Austin
- Miami (tie)
- Cleveland (tie)
- Boulder (tie)
- San Francisco (tie)
Yes, Cleveland (4,2) tied San Francisco (9,7).
Surprisingly, I’ve found more cities are underrated, probably because I had an exceptionally fine experience:
- Philadelphia
- Madison
- Asheville
- Ottawa
- Minneapolis
- Richmond
- Newark
- Buffalo
- Providence
As always, YMMV. Based on visits mostly within the past decade.
west north 
I was really looking in your chart for Austin (because it seems to me to be clearly the most overrated city), but couldn’t find it – then I saw that it made your list of most overrated as well, and for some reason just doesn’t show up in the chart, even though nothing else is overlapping it. After four years in College Station (halfway between Houston and Austin), I’ve come to the conclusion that I like Houston and Austin approximately equally (it’s possible Austin gets a slight edge), but as a result, Austin seems to me to be the most overrated American city, and Houston one of the most underrated. (I agree with you that Philadelphia and Minneapolis are also quite underrated.)