Massapequa, NY, United States

With a population of just over 21,000, Massapequa can feel like a sleepy suburb - but don't let the quaint facade fool you. This Long Island hamlet has weathered its fair share of storms, both literally and figuratively. The tax burden is heavy, and the bureaucracy can be a persistent headache, as evidenced by the town's long and complex history with local school districts. And while the Atlantic Ocean provides a moderating influence on the climate, Massapequa is no stranger to powerful nor'easters that can knock out power for weeks on end.

Still, the town does have its charms. Massapequa's close-knit Italian and Jewish communities give it a distinct cultural flair, earning it the tongue-in-cheek nickname of "matzah pizza." And with a median household income over $179,000, it's clear the area attracts its fair share of affluent residents. But for those seeking an easy, carefree lifestyle, Massapequa may not be the best fit.