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I would never live in Orlando, or FL for that matter. The crime rate is very high, substantially higher than Boston. And Boston is a real city with real city problems, yet the crime rate is lower than Orlando. The Greater Boston area and suburbs has remarkably low crime.
Disadvantages:
Orlando: hurricanes, mickey mouse culture, palmetto bugs, high crime.
Boston: Blizzards and nasty winters, very expensive, older housing stock and infrastructure
Both: idiot drivers and traffic
Advantages:
Orlando: nice weather if you like it hot, beaches.
Boston: schools, museums, sport teams, a real city, four seasons if you like that sort of thing (granted the only really good one is fall), proximity to mountains and nice beaches.
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