Annapolis, MD, United States

The tax burden is heavy, and the bureaucracy is a persistent headache for those moving to Annapolis. Annapolis High School, part of the Anne Arundel County Public Schools system, was ranked the 16th best high school in Maryland in 2010, with a rigorous International Baccalaureate program. However, the school faced a controversial "zero-basing" reform in 2007 that saw around half the teachers and staff let go. While the school eventually met academic standards, the tumult is a reminder that life in Annapolis is not all historic charm. This city is best suited for those who can navigate its administrative complexities and aren't deterred by the occasional bureaucratic challenge.