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I'd say River Market area or the Plaza.
The River Market seems really unique to me. It has great lofts, and while it's not downtown, it's very close to the entertainment and nightlife of the city. Lots of great restaurants (french food - le frou frog, a hugeeee chinese market, succotash and cascone's - great breakfast food, bo ling's, delaware cafe...). It's generally safe. People seem to have a neighborly feel like a suburb, but looks or otherwise feels nothing like one.
The Plaza is more upscale and it costs more. The bars follow the same pattern. Lots of shopping, some reasonable, some not. I don't think of the Plaza as crime ridden by any means, but I vaguely remember an old lady getting attacked in a parking garage a few years ago. Here, you'll also be close to Westport's bars.
Apparently Westport's crime is getting worse (robberies, mostly), however I've never felt unsafe. I always take a cab from the bars rather than walking or riding my bike. As far as what you're looking for as entertainment, this will be the best place. There are a lot of dives & music venues.
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