The bureaucratic red tape you New Yorkers are forced to cope with is ridiculous! In Florida, an 18 year old can own a handgun and keep it loaded and "securely encased" (in glove compartment) as he or she drives without a concealed weapons permit. You must be 21 to buy a handgun though. The New York politicians have constituents demanding the disarmament of their targets to ensure their loot. I say move to Florida. I'm 21, and within a few week will have a CCW permit and would NEVER visit a state I could not carry in. I feel so bare and disarmed without being able to carry right now. You could buy a few guns in Florida and then drive up to NYC... Not sure if that is illegal.. But since you have no chance of being able to carry in NYC you might as well get a rifle and carry it over your shoulder with a sling wherever you are on your property.
Good luck