Let me answer some of the questions:
There are 2 types of permits in NYC, premises permit and a carry permit.
Premises permit is not that difficult to get, although it requires a squeaky clean record (not even a moving violation, no debt of any kind, whatever the criteria is), several visits to NYPD Pistol Section, an extensive background check, a personal interview with a detective, fingerprints, and a $500 check.
A carry permit requires (in addition to all stated above) a "good cause". One has to prove he either carries large sums of money (I believe $25,000 min), or has documented threats against one's life. Plus, NYPD comes out and talks to your neighbors and co-workers whether it's OK that you have a pistol permit. So you better hope your neighbors like you. You also have to provide a notarized statement from your spouse that she approves that you want to have a pistol. Unless all these things come together, you will not see a carry permit. That's why out of the city of 9 million, only around 2,000 people have carry permits, and that includes retired cops and armed guards.
There's hope, however. The 2nd Amendment Foundation is suing New York to throw out the "good cause" clause as unconstitutional. Hope it makes its way through the courts soon.