I can help! I lived in Brooklyn for 4 years, in the early 80's.
How fab a hotel are you thinking about? My absolute favorite is the Waldorf Astoria. It's very "old elegance", the rooms are snug and have personality, and Peacock Alley (with Cole Porter's piano) is THE place to relax and people watch. Their restaurant, Oscar's, is wonderful, too.
My favorite upscale restaurant was Lutece, but to my sorrow it closed this past February . So many restaurants have come and gone, I'm not even going to try to suggest one, but for a slice of history and an awesome view, there's always the Rainbow Room at Rockefeller Plaza. For less opulent places, my absolute favorite burger joint is Jackson Hole, on 64th St. between 2nd & 3rd Ave. (And I checked, it's still there and still getting "best of" awards left and right.)
Let me know what else you're thinking of doing, and I'll see what I can come up with. I'm an expert at doing NYC on the cheap, but was also blessed with an extravagant lover when I lived there, who showed me all KINDS of wild stuff I could never have afforded.
KarenK