re: The view from my "office"
I think of NYC is a city of neighborhoods, rather than the 5 boroughs. Recently I have been spending plenty of time around the Lower East Side, East Village and Williamsburg which have rapidly gentrified and are now rather trendy. Although the hipsters are starting to take over some areas which is a bit of a turn off for me, but I find them less w@nky than in Australia. Generally speaking anything around NYU is quite reasonable - Union Square, West Village, etc.
The best nightclubs tend to be around Meatpacking, Chelsea, Hells Kitchen, and increasingly over in Brooklyn.
I still really love the Gramercy Park Hotel. I'm sure hotel experts will list better value options, but the history, stories and location mean I rate it highly. It probably helps that the hotel was packed with Russian Supermodels the last time I visited. NYC has several iconic hotels which you can stay at - The Waldorf Astoria, The Palace (Gossip Girl), The Plaza (Home Alone 2), etc.
For the first time visitor I would probably stay in Midtown, and if you have hotel chain points, it is often a good place to burn them. Midtown itself is a little soulless, but it is fairly central to get around to most of the postcard type attractions you are likely to want to see on a first visit. Another option is AirBnB, although many hosts charge hotel prices now.
It probably deserves its own thread, but beyond the postcard views, the scale of NYC is immense. There is heaps to see and do, whatever you are interested in.