Every farmer and landowner I know and get permission from like that I am early to ask, always respect their land, never leave a trace I was there (well, maybe a few blood drops from my harvest) and follow any reasonable request of theirs.
For upland game and waterfowl: I have all of my written permissions already. I started getting those around July 1st. One farmer I know I visit him on Canada Day as a "Thank You" for the past year's permission, then he'll make me another written permission good until the next Canada Day for anything I want to hunt on any of his corporate farm he has.
For large game hunting with a bow, I also have that permission already: started that in August, but that was a short list to talk to.
For large game hunting with a rifle I am working on the last one or two permissions now.
When they are done there are a few farmers that won't let me hunt anything on their land... except coyotes! But they let me hunt them any way I want from Boxing Day until the last day of February, so I'll be visiting them the first weekend after big game season is over (that visit weekend will be Dec 5th this year).
Edit: I almost exclusively hunt birds and large game for food to feed my own family, including helping my aging parents get out there and fill their freezer. My hunting is about eating, feeding my family, so I make sure to get permissions early and maintain the best sources of hunting land: half of the farms I hunt on my family is the only ones to get written permission and always get priority. Good will and kindness goes along way.