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If you really live in Brooklyn you might get the most bang for your buck buying an "old-fashioned" ti bike with rim brakes and clearance for only 27mm tires with 10 speed group. It's hard to find a hill on Long Island so you don't need disc brakes and 11 or 12 cogs. A nice MOOTS, Serotta, Hampsten, Erickson, Lynskey ti bike will NOT hold you back in the rides you have described and even if you "lost" 1/2 in a future resale it would only be a few hundred bucks at most.
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