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 :)