I never lived in such a development, but I lived thru the period in which they were built (b. 1937 -- too young to be a beatnik, too old to be a hippie), and I can remember some of the circumstances & the literature. The mass production of housing was to a large extent a rational response to a situation in which little housing had been built during the depression & almost none during the war, and the veterans came home & started families & wanted housing, and the economy had recovered & people had money again. Some of the consequences well deserved criticizing & satirizing: see Riesman's _The Lonely Crowd_ & Keats's _The Crack in the Picture Window_.

The uniformity of housing developments was also, of course, symbolic of the conformism that was rampant in the decade after the war -- the idolatry of Society. Independence of mind was widely thought to be impossible (you were either conforming to a subculture of deviants or merely being perverse) or a symptom of mental illness. Fortunately, there was also a great deal in American culture that was at odds with the glorification of cowardice (Emerson & Thoreau were still read in the schools), and it couldn't last. On the fringes, besides "Little Boxes", there were Mad Magazine & the scathing sf stories by Kornbluth & Pohl. So then we had the silly '60s, which were a relief from the stuffy '50s, which were a relief from the bloody '40s, which were a relief from the dirty '30s.

(For me, incidentally -- and perhaps even for Malvina Reynolds at the time -- the primary meaning of "tacky" is slightly sticky, like paint that hasn't quite dried, or an asphalt road on a hot day.)