I lived in Chicago for 5 years, San Fran area for 10 years, Los Angeles for 7 years, and Kansas City for about 8 years. I have to say that SF is probably the dirtiest, at least in parts, though Chicago always felt kind of rust-belty in many parts, rather than dirty. In KC, cleanliness tracks money more closely than any other place I've been. The Southwestern cities have always struck me as the cleanest of the places I've been outside of Germany (at least 30 years ago), Switzerland, Canada, and Monaco. Phoenix, Tucson, San Diego, Dallas, San Antonio, Albuquerque.

The other big problem with SF is the parking. Horrendous. And yes, many of the people there do seem to spend a great deal of time in an advanced state of self-congratulation.