It's not that different, depending how far north you get in Manhattan. The distribution of housing types might be different, but things get pretty residential in the northern end of Manhattan, and you're as far away from "midtown" than those places are from downtown SF.

It's as far away geographically (even further for the north in terms of miles), but even if you get to harlem/university heights the types of buildings and the way the streets feel is different from the sunset/outer richmond. There is just some sort of gloom and emptiness because of the density of people & climate in those neighborhoods compared to manhattan. You'd hardly find a street in manhattan that has the feel of this : http://foundsf.org/images/2/23/Photo9Ungaretti.jpg

Maybe the light colors in San Francisco's outlying neighborhood's architecture make them look just even more distant and quiet / abandoned?

Also, the ease of getting into the heart of manhattan (say Union Square for both cities) from north Manhattan just feels different than taking the Muni/Bus in SF. You're inside the subway, enclosed and underground. The neighborhoods that have that distant feeling in NYC are ones like Flushing, Gravesend & Jamaica. Or Canarsie. Canarsie is so far away...

Also, Hi Tom - This is Alex from the first Stuy meetup :)