It took me all of 24 hours living in New York to realize that it's not a user-friendly city. And by this I mean, if you don't just KNOW what you're doing, good luck figuring it out, cause there is very little (structurally) that will aid you in this process. First of all- finding a place to live. I fortunately didn't really have to deal with this, because I just moved in with Lindsay, but if you've ever talked to anyone who tried to find an apartment in NYC and/or dealt with a broker, they invariably have a story that involves stress, anxiety, and a complete sense of frustration with the system. Check out "Housing Virgins of Manhattan" for futher evidence of this.
Riding the subway is another one. It's not such an intuitive system, especially when comparing it to... ANY system in european cities. Which trains are express or local? And why are some express sometimes and local other times? And if you don't happen to know that brooklyn is south of the city, how would you know which way "To brooklyn and Coney Island" means? And there may be one map somewhere in the station, if you're lucky. But it's likely not where you are.
Or try driving around this city, especially South of Houston- forget about any attempts to figure THAT out, cause it's just nuts with streets going every which way and no signage. Want to get to a bridge or a tunnel? Nope, sorry, no signs. Or say you're in Brooklyn driving and want to find the highway, nope no signs... oh wait, there was that one tiny small one hidden by a tree...
And to further complicate this situation, everywhere you go there are hundreds and thousands of people around you going in hundreds of directions, all of whom appear to know what they're doing. Take any of the major train/subway stations- man I would HATE to walk into one of those places if I had never been to NY, or worse, was travelling from a foreign country and didn't speak much English.
You are simply swept up into the hustle and bustle, and you better be ready for it... 5 minutes ago. Know what you want to order before you even walk in the door of that deli, have your money out 3 people ahead of time in line, and heaven forbid you don't know which way to swipe the Metro Card, cause there are 5 people waiting right behind you who are late for something.
However, despite this lack of user-friendless as far as the structure of NYC goes, I will say that New Yorkers themselves are more than willing to help out anyone who needs assistance or has a question. You may not know how to get somewhere on the subway, but there are 10 people standing around you who do. Or you may not be able to figure out how to get on the I278, but the fireman who has lived in Brooklyn his whole can tell you an even better way to go.
And that is at once the beauty and cruelty of learning to live in New York City.