As many have said, rust will be an issue for you. Try and find a non-rustbelt truck to start with. Back up camera and screen is better on the '17-'18 models, and those years will hopefully have less potential for rust sicne they are newer. I'd only go G63 or G65, but that's because I've become accustomed to 500HP-700HP in just about everything I drive. Springs and shocks can help with the harsh ride, and it's actually relatively cheap to lift them and put larger tires on them when the time comes to go offroad in Europe. G65 is out of the budget you outlined, but if you ever drove the V12 you would be hooked!
Find the lowest mile, rust-free example in the color you want that is from a state that doesn't salt the roads. Get a pre-purchase inspection done (and tell the inspector where to look for rust problems if they aren't already familiar with Gs), and then start to enjoy it. Shian gave good, real world info on driving in NY. Sounds like a total pain, but if you gotta drive in NY you might as well do it in a G!