Keep the Kimber Montana 308 , and put the Zeiss on it.
Keep your Rem 1100 outfit. I'd prefer a 20 gauge pump outfit, but that is my view, not yours.
Sell everything else. You have NY game covered with the above two firearms. Shoot them as much as you can.
I'd pick up an accurate 22 LR for squirrel hunting. Doesn't have to be premium, just accurate (I like bolt actions). If you want to go chuck hunting a 222/223 bolt with heavy barrel and 6x scope is nice (is Howa 1500 varmint).
Then buy a recurve bow, and have a lot of fun. Southwest Archery Spyder XL 64" amo bow ($150), 30-35# draw weight, some Easton Tribute xx75 aluminum 1816 or 1916 shafts ($3/each at Lancaster Archery), and get "Shooting the Stickbow" by Anthony Camera ($20).
