Congrats on a fine dog.
Two things about Chessies. First, they are very protective. Any agression must not be tolerated. You need to nip that in the bud quickly lest you find yourself hunting all alone as you are the guy with the ill behaved dog.
In addition, work dilegently on socialization. Take him everywhere, and I meann EVRYWHERE with you, always on a leash or P collar.
Chessies have a somewhat misguided reputation for being hardheaded and needing a firm hand.
I have a have a friend who has one of the most well mannered Chessies that I have ever met. When I asked how he managed to get the dog through training, he told me that with Chessies, you have to make the dog think it's his idea. Keep your training fun. Work under the theory of "puppy games".
Chessies are beautiful dogs. When the weather gets really nasty and frigid, my money is on the Chessie to get it done and never complain.