Congrats Greek:

Before checkin on seeing about other hunters, it would probably be the best bet to meet the guy and to fill your tags first, not to be selfish but I am sure once you get a better feel for the landowner and he is comfortable with you then it might be a better time to ask. But just offer to help out around his place and when you do get that deer which I know will be soon, offer him some venison. Usually I also send them a thank you note after the season along with a card around the holidays just letting them know I appreciate the use of their property and it shows you are caring and respectful. Goodluck!!