My Choice
With only one platform to work with you need something that can fire more than one type of ammunition, including .22 LR if at all possible. When I bought my first handgun I had similar criteria, but for different reasons; I wanted a durable, higher capacity gun that used a military round and had readily available parts that were easy to install. Thats why I chose a Beretta 92FS Stainless (INOX) pistol.
This is part of my setup:
Other advantages:
There is a
Factory made .22LR conversion kit available... if you have the $$. (~$400-500). This kit is made for precision shooting with adjustable sites, but having shot some 4,500 rounds of 1-2 CENT ammunition through it, the mechanical tolerances are not so tight as to cause many malfunctions. Most misfeeds are due to soft lead bullets being caught on the feed ramp due to misformed projectiles (i.e. they're cheap).
Magazines and Parts can be ordered from the factory or easily found online from aftermarket suppliers. If you have any mechanical inclination you can break this pistol down to bare frame with little more than a nail, paper clip and flat head screw driver. The slide is more complicated, but with steady hands, and alittle ingenuity, then extractors, firing pins, etc. can also be replaced with ease (not that I have had any failures of these parts even after 10,000 full power 9mm reloads).
With your funds I recommend searching for an original italian made 92FS INOX. IIRC these can fetch $800-$1000 alone with another $50-100 per original stainless mag. You will certainly want the conversion kit, but expect to wait 3-4 months as they are highly sought after. Additionally, look for a nice leather holster in case you ever need to use the thing in the "urban jungle" so to speak. Don't buy cheap nylon gear like those Mike's ones either, they break down and aren't very durable.
As far as ammo goes, look for case quantities of factory ammo to begin with. Avoid wolf brand altogether for this gun.
You should also buget for another $100 for cleaning supplies, a nice hard case and targets. I suspect range fees in NYC are also pretty high.
If there really is a magazine cap limit of 10 rounds in NYC, then you should take the advice of the guy with the .45ACP w/ the .22LR conversion and 9mm adaptor thing. You can't go wrong with .45 ACP, I just prefer the double magazine load that the Beretta offers.
EDIT: Darn there's a 10 round limit in NY. Maybe you should consider a compact XD-45 with 10-rnd mag. The 1911/22/9mm option would probably be best tho.