Cupertino, CA, United States

Cupertino's population of 60,381 may seem modest, but the city's sky-high cost of living makes it a tough sell for all but the most affluent residents. Housing prices have reached absurd levels, with the average single-family home starting around $2 million. The local economy is dominated by tech giants like Apple, but this has come at a cost - the region's notorious bureaucracy is a persistent headache for businesses and residents alike. While Cupertino enjoys a warm-summer Mediterranean climate, its isolation and lack of public transit options can be frustrating. This city is tailored for the well-heeled tech elite seeking a slice of Silicon Valley's prosperity, but its steep price tag and limited amenities make it a challenging place to call home.