Actually I think how the city is layed out is an accurate depiction. If you don't think so, try driving around Boston for a day.
The bigger problem is how the numerous quests in the area were designed. Someone with a warped sense of humor designed them to cause the maximum amount of frustration. While that might be what its like to truly live in a city, it doesn't necessarily make it fun. If a little more thought had been put into the quest design then the area might have been a lot more fun rather than bordering on tedious.
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