Most of the time, you might as well go home as hunt upwind of deer. But, I think that during pre-rut and the rut, you can get away with it if you are really careful with your scent and use attractant scents. In '99, hunting public land in Illinois, I found a spot like the one you describe. It was on a point, on the edge of a small cliff. The wind blew right to a big bucks bedding area from the only woods with trees big enough to hunt it. I had no choice but to come from upwind and hunt upwind of this buck. So, I was EXTREMELY careful with my scent, I loaded the area with doe-in-heat scent, AND I used a cover scent. This buck came in just after first light to a film canister, and the rest is history. My guess is that if I found this situation 10 times, probably I get this buck 3 times, and 7 times I scent spook it. But sometimes it works if you play your cards right....