I have never hunted Kentucky but wanted to say I love the way you worded your original post. Every thing you said is the true essence of what hunting is all about.
Here is my advise assuming you don't have private land to hunt (all I hunt is public and in multiple states).
Google public hunting lands close to where you will be. Download the hunting regulations and license info, etc.
Then use google earth to get a look at the land. Then use mytopo.com to view the topo maps of the area. If possible print out a map. Mark off areas where other hunters will most likely go, areas that deer won't want to go, and areas that don't offer deer anything to use.
Then start looking at the rest to find funnels, pinch points, food, bedding, travel corridors, etc.
When you get there head right to those good spots and verify fresh sign and start hunting when the wind works for each spot.
Then post the details and pics of your amazing adventure here for us to enjoy as well.
If you need and more help on how to plan it just ask. I live for this style of hunting... Always a new place and a new adventure.