Well, ya never know. Sure, it gets a big push in the movies and such, but who knows if it’s going to turn out to be Hicksville. 
I spent a week in NYC during spring break 5ish yrs ago. I had bought new walking shoes for the occasion, but they weren’t broken in and I ended up with the most hellacious blisters after day 2.
We were on a VERY tight budget, but my bf-at-the-time and I managed to book a hostel-type situation that’s only a couple blocks from times square and was less than $100 a night for a shared room (likely more pricey now, given inflation, but still cheap as flimsy buttons, considering the location). It had 3 shared bathrooms per floor, but they were single bathrooms (not like a communal shower or anything). It was a very repeatable experience if your budget is shoestring (we were both college students). I wish to god I could remember the name of the place. They book up crazy far in advance, but more than a year out you should be able to find a space there.
I recommend you plan at least a loose itinerary. I had to make a tight one, since we wanted to try a little of everything and our budget was quite finite. But we had a definite list of restaurants we wanted to try (there was a fantastic tiny Ethiopian-cuisine place which I remember very well, but not the name [of course]).
Back then the nightclubs in NYC weren’t very well-documented online–perhaps that has changed now. We had a list of 5 we wanted to try, and only 1 of them was still open. We happened to go on their gay dudes night (didn’t know that until we got to the door, and we weren’t turning around for anything!), which was actually a lot of fun for me since there were only like 6 girls in the entire place (presumably they, like me, didn’t get the memo beforehand). And the guys there were all either the dates of those 6 girls, or looking for other guys, so I didn’t feel pressured to look good, didn’t have to worry about getting hit on. We boogied our asses off!
Is There Anything to Do in NYC?
Eat.
Calvin Trillin once noted that when outsiders asked why he and his wife continued to live in New York City, he explained that they were big eaters.
Why, I bet you could stay there a month and never eat in the same place twice. 
I could go for a month and not eat in the same place twice where I live - even assuming I have to walk to the restaurant. In New York you can go for a month and not eat the same cuisine twice.
Eating. Oh yeah. We can do that. 
It’s not. You can pretty much find something to do all the time, every day of the week.
Just don’t fall into the typical rube trap of getting confused, going to Times Square and going to the same Applebees and Olive Garden restaurants you would go to back home just because they have 60 foot neon signs.
Good to know we won’t end up sitting around twiddling our thumbs.
We plan to keep the entire month – NYC and Hawaii – at under US$10,000 but won’t be too put out if we go above that a little. Half of that will probably be airfare – Bangkok-NYC-Honolulu-Bangkok. One helpful factor is the baht, our local currency, has strengthened so much in recent years and shows signs of strengthening further this year. What would have got us $8000 five years ago will get us $10,000 today, a big help. Just hope it really does stay that way.
As a former long time resident, I’m going to strongly advise that you venture out to the outer boroughs for at least one day, or make a trip out each day. By only going to touristy places, particularly midtown and the financial district, your stress level will certainly rise due to the sheer mass of people (longer waits for everything, and more expensive), and it is in these places that you’ll be more likely to encounter the “rude” NYer.
The Bronx, where I lived for 5 years, has got a wonderful Little Italy, locally known simply by the nabe’s main street, Arthur Ave - it’s got restaurants and bakeries aplenty. Close by are The Bronx Zoo and The NY Botanical Gardens. An added bonus to these particular sites is that they can be reached by taking a commuter train out of Grand Central Station, which you absolutely need to see anyway. The Bronx also has a famous baseball stadium that you may want to visit.
Take a stroll over the Brooklyn Bridge, then catch a cab to Cobble Hill, Carroll Gardens or Park Slope and then just walk around - plenty of pretty brownstone buildings and tree lined streets dotted with boutiques, cafes, and restaurants. Further north in the city’s most populous borough you’ll find Williamsburg, which has been THE neighborhood for hipsters for the past 10 or 15 years, and there are lots of smaller art galleries that exist here. One subway stop away on the L train, you’ll find Greenpoint. Other things to see in Brooklyn include the Promenade (best view of lower Manhattan here), Prospect Park, the Brooklyn Academy of Music, the Brooklyn Museum, and if you’re feeling adventuresome you can see “Little Odessa” in Brighton Beach.
I’m not too keen on Queens, though there are some neighborhoods that you may like, Astoria is the one that I would recommend - historically predominantly Greek populace.
Staten Island is not without its charms, but unless you have a car, you won’t likely make it here, though I might suggest The Staten Island Ferry if you’ve got an hour at your disposal - some very nice views.
In Manhattan, there are obviously certain hotspots that you’ll want to see, but if you go to the same places that everybody goes, imho you’ll end up seeing fewer things. Some alternatives - up at the northern end of “The City” (as Manhattan is sometimes referred to as) sits Fort Tryon Park, where you can visit The Cloisters, a branch of The Met that’s devoted to art and architecture of medieval Europe. You could probably spend all day every day between 23rd and Houston or Canal and have an amazing time - there is so much to do in these neighborhoods - Chelsea, Gramercy, the East Village, the West Village, the Village, the Bowery, Nolita, the LES, Soho, Chinatown, and Little Italy. Look into each of them on line (15 months should be enough time to get a good grasp), and spend a day in a few of the ones that grab you the most.
Look over the subway map, and the bus map as well (good for crosstown travel in certain areas). Manhattan is a grid, pretty easy to figure out.
I do hope that some of this helps, Sam, you gave me terrific info when I visited your hometown a few years ago, and for which I am grateful.
Nah, that’s out on Long Island.
He is talking about April of next year.
Yes, April 2012. I’ve never actually seen The Daily Show. at least, not a full episode. Clips here and there. I think it’s on cable here, but we are too busy to watch TV so don’t subscribe. But I know of it and would see it and Letterman. Is Johnny Carson still on? (Just kidding. :D)
Thanks again for all the suggestions. This is all very helpful.
Great ideas above. Some other ideas for stays - many renters sublet their apartments for periods they are away; check Craigslist or Backpage.
April = NY Yankees
Central Park:
-
Check out the setting sun view of Central Park from the third floor of the Time Warner / Columbus Circle building 59th and 8th Ave (aka Central Park West).
-
Horse carraige ride through Park - 59th and East Dr
-
Eat at the Boathouse in the park north of 72d Traverse on East Dr.
-
Check out the roller skaters on he 66th Traverse at midday on Saturday - yes, many in 70s and 80s costumes, short shorts and many a 'fro
For things to do, keep an eye on Time Out NYC (newyork.timeout.com) - lists all kinds of events happening in all boroughs and times of all shows
Catch out the street artists in Union Square and Washngton Square Park
Walk across the Brooklyn Bridge (~.75m across)
Charging Bull in Bowling Green Park by Wall Street
I’m sure you’ll get many more ideas for awesome things to do in my favorite city! Have an awesome time!
You might want to check out the High Line on the West Side. Basically they turned an old El train line into the worlds narrowest park.
Manhattan isn’t as big as you might think. If it’s nice out and you have the time, you can pretty much walk from Times Square down to Battery Park in an hour or two.
We were thinking B&B but have heard something about a new city law – real or potential, not sure – that would make many of these apartment lets illegal. Does anyone know what’s up with that?
Well there are a lot of ‘illegal’ hotels and such in the city. More like a legal gray area.
But enforcement is difficult due to the number of apts in the city.
What I want to know is who is going to watch the pigeons? Maybe Mike Tyson?
There is a state law effective May 1, however, the properties affected are overwhelmingly already illegal.
http://therealdeal.com/newyork/articles/time-s-up-again-for-illegal-hotels
But Zebra is right. Enforcement is erratic. However if you are one of the lucky ones caught in a bust you will be out on the street.
I agree with those who commented that one may not wish to stay outside the city. I’d include anywhere in Manhattan as within the city, and if you’re hardy, it’s easy enough to walk from, say, anywhere in Central Park to downtown, if you enjoy walking.
It’s been ten or twelve years or so since I lived in Manhattan, and the few times I’ve wandered through to visit friends or catch a plane, it’s changed a bunch. I’ve stayed lots of times in hotels around St. Marks in the E. Village, and also lived for about six months as a student at a hotel in midtown, and also have lived for a few months with some acquaintances on the Upper West Side, among lots of other places (I’m just listing my transient addresses) – it’s all good, and I don’t see any bad side to any of these spots, especially WRT transportation to anywhere else in the city.
I was going to cite the Sarpedon vase (“krater”) at the Met, but a quick check on wiki revealed it to have been repatriated to Italy recently. There are still some good Sargents on display, though.
Guess we’ll have to wait and see and gauge the B&B situation at the time. Still 13 months away.
It turns out the wife has a friend there who was back here for a visit recently. She and her husband are Thai but both Americans now. They have a big house somewhere on Long Island, dunno where yet, and say they’re always putting up guests. They want us to stay with them, but I’m not very hot on the idea, nor is the wife really. For one thing, the lady insists two days is more than enough to see NYC. This could be one of those typical Thai thinggs – they often opt for, say, the half-day guided tour of Angkor Wat when one could spend literally weeks exploring the huge and far-flung complex. Then there’s the question of staying out late. Don’t even know where on LI they are. We’ll probably say no.
Heh! Poor little guys. It’ll be good for them to hunt for a while. We deserted them last year while in Vietnam and will be gone for a few days soon. I’m sure it’s always a shock to discover the cafe is closed. 
Wow - yeah, two days is NOT enough to see the city.
Not to mention, if you really want to do the tourist thing, it’s best to be in the thick of things right there. You could always spend the 2 days with the friend, THEN go stay in the city :).