I have bow hunted for white tail in Illinois quite a bit, until I moved.... We hunted many small timber pockets like yours, and there arethree basic pieces of information I would share on the subject.

Firstly, It doesn't matter where the stand is, as long as the wind is right when you sit there.

Second, the first 2 or 3 times you sit on a stand are going to be your best opportunity to kill a buck, so don't screw with marginal wind conditions.

Thirdly, truly trophy/choker bucks (Booners), don't always hang in these timber pockets. These old monarchs have figured out that a drainage ditch or a fence row out in open country is where it's at for safety. They come by these timber patches after shooting hours and before light, scent checking things from the feilds. If the rut is on, and you have used the wind right, a big boy might slip up and visit your shooting perimeter.

Good luck