But I'm the luckiest guy on the Lower East Side
Having been taking (strictly) amateur photographs in New York off and on for the past 3 years, I gotta say, DUMBO in summer is probably the most challenging neighborhood because it's so hard to manage light there. It's not like Yosemite where pretty much anyone with a disposable can come up with a pretty decent picture, if not the same calibre as Ansel Adams.
The midday sun is a little too intense and washes out colors where it's sunny, but because the streets are so narrow and buildings are close together, the shades end up being too dark.
You can wait for the late afternoon when the light is softer, but then you have the problem with the shades again.
Plus, all the major landmarks have been photographed to death (see below) so you have to walk around to find a unique angle.
Of course, that means if you do come up with a great, original photograph, the effect is that much more dramatic. But alas, I haven't figured out how to play with light and shadows well enough, I don't have a strong eye for details and my composition is astrocious.
So I guess it's not so much that DUMBO is challenging, it exposes my shortcomings as a photographer. Still, there are much worse ways of spending a weekend afternoon than riding around looking for something that could make a good photograph.