RE: How do i hunt him
Your blue dot looks like a likly spot as does the green east-west strip between the fields if the wind is out of the east-north.
Here in Iowa, the winds tend to be at least partly out of the west.
I can't tell by your drawing if there is a north-south fence line on the east edge of the property. If there is, I would use it for a bit for breakup cover north of where the trail enters the corn field. It looks like you should be able to shoot towards the west or south from there, the spacing around the buildings should be ok from a half mile away. Just keep them in mind when you shoot. Hunting from the east edge of the property should give you more wind direction options.
Bob