Not enough info to answer your question in detail, but in general I would suggest that you not go into the timber any further than necessary. I used to hunt a tract of about 20 acres that was completely surrounded by tillable ground. No roads. Always held deer, and the trick was picking where they would come out in the evening , or go back in of a morning. If you hunted mornings only you might get away with looking for a perfect spot deeper in, but in my opinion that would result in busted deer if you tried that in the afternoon.
Google Earth is very helpful when trying to determine what the deer may do and why. Find your area on the site to see how it relates to surrounding cover and food sources. Use that info to search for a heavily used trail near the edge, then hunt it. You should see fairly quickly if you've chosen a good spot or not.
What county are you in? I hunt around Peoria, Fulton, Tazewell and Mason counties.
Good luck!