Underrated observation. S.F. has always had a scraggly personality since the Gold Rush days. It's where Dirty Harry and tons of '70s police procedurals were set in, after all. The issue is that despite tech wealth since the late 2000s, none of it has seemed to better the city and in some ways has increased wealth inequality.

Manhattan's answer is because of Giuliani's authoritarian mayoral reign. Cleanliness came at a cost of mass arrests and evictions of the homelessness, restrictions on shelters, and stop-and-frisk. Probably not a price that S.F. is willing to pay.