I think Boston's issue is exacerbated by it's geographically small size. Urban renewal erased scollay square, the city did everything in it's power to gentrify the combat zone and the surrounding theater district, BU took care of Kenmore Sq., Landsdowne St went corporate. The area around North Station is increasingly filling with residential use. Many of the areas that would have been hospitable to a growing nightlife scene are no longer available. Further, the remaining core neigborhoods, Beacon Hill, North End, Back Bay, S. End., Southie and the North End are all densely residential and well organized to resist the development of a budding nightlife district full of noisy bars or clubs.