CM ... what makes you think that training a retriever for upland is done any differently than a spaniel or other non-pointing breed " upland dawg" ? You are correct about teaching waterfowl retrieving skills first, however.

There are NAVHDA Clubs around you and that' s what you are trying to accomplish, making that Chessie a " Versatile" dawg. Look into joining one and getting help there ... http://www.navhda.org/chaptmap.html

Of course ... you could always try to train him like my yellar dawg who has this peculiar habit of getting very stubborn, freezing in place and refusing to move when hot on a gamebird ...