These lines of Frank O’Hara keep coming back to me as we hunt for a new place:
“I can’t even enjoy a blade of grass unless I know there’s a subway handy, or a record store or some other sign that people do not totally regret life.”

Me too. My word problem for the perfect apartment involves drawing a polygon with points joining a public library, a coffee shop, a movie theater, subway stop, and a place to go on a long walk. Fill in the area, and put a dot more or less in equidistant from all the points. That’s where we want to live. The rub is, for city people at least, that’s where we all want to live, and the premium is high.
Walk Score does a version of this (although its algorithms are a little shaky). But there’s something missing, that sense of how you feel about a neighborhood as you leave or come back to your place. As an architect friend of mine points out, this is perhaps the most important ingredient, and one, unlike the inside of your home, that you have very little influence over.