I wear some of my clothing while driving then put on the rest when I get out of my car. You can really go nuts over scent control but all I do is wash my clothing and put scent spray before I go in the woods.
Well you need private land to hunt most of Westchester so you may have to start knocking on some door's. I doubt youll find someone with 10 acres but I always see deer in the areas your talking about, so its worth a shot.
Welcome to the site. Its a great place to learn some local knowledge for hunting in NY. Although you wont find too much about public land so you'll be on your own for that. You could speak to a dec agent and ask them where to start looking.
I don't think you need to put 200 rounds through your gun, in fact most people don't put 200 rounds through their deer rifle. A box of 20 should suffice really.
I rarely use a mask and never any paint and its not as bad as you think. I don't have loads of deer or very many deer spooking when they look at me. I probably will start using some face paint but its not as important as people make it out to be.
Ive never seen a bear yet or hear of any in the area. I know eventually they will start showing up in the area. I know one was shot close to the property I hunt in 3J but still no sign on the property its self.