In my opinion it is impossible to always have the wind in your favor entering or exiting a treestand. No one can predict with total precision where all the deer will be. Maybe once on stand, where hopefully you have a very educated quess based on scouting, sign and observation of activity as to the approach and departure of the deer. But walking to a stand (unless you are parking within a hundred yards) you cross so many travel corridors that deer use that its impossible to know all of them. Some stands that I have are at least a 30 minute walk from where I park to where my stand is located. Even if I knew every deer trail between those two points what could I do about it. The things I try to do is remain as scent free as possible by using proper scent control and not touching anything with my bare hands while trekking to my stand and try to remain unseen once I get to the area my stand is located and for that matter on the way there. I take extra time to glass fields before I cross them (including the wood lines) and then I walk to my stand and hunt. My path is not a straight line because I hunt in hill country and the old logging roads I follow dont go in a straight line. They follow the terrain. They switch back and zig zag as they will. They switch so often that scent eventually has to blow in the wrong direction. Approaching a stand situated below a hillside the deer are bedding on would in my opinion be far worse because every deer on the hillside are watching every thing you do. If they are bedded over the other side where they would not see you approach you could do as you have said and walk through the field to your stand, But my quess is they will be overlooking that field. In the morning with a very quiet and slow approach under the cover of darkeness I think you would be amazed at what you can get away with.