Step #1: Buy a deer rifle and a scope. Cost: $400 for a standard Wal-Mart .243, .270, 30-30, 30-06, 300 mag, 7mm or whatever is fine. Don’t worry about “best gun” to be used on a Kentucky deer hunt. The differences just don’t matter and they all will do the job. As far as a scope (known as optics for people in the game) cost: $60 and you’ll be fine. I have 6X18 Leauopolds, 44 fixed, Swarvoski, etc. I’ve paid more for scopes than I have cars. They aren’t needed for Whitetail Kentucky deer hunting. If you want to be “cool”, buy a 6.5 Creedmoor, it’s trending as being the most accurate long-range rifle if you’re into measuring differences by parts per million. Buy 20 rounds of ammo and use half of it to sight in your scope to get you through this year's ky hunting seasons.
Step #2: Research Kentucky Hunting Outfitters in a Kentucky hunting forum. They all are likely good guys, but not all are equal. Take a wild guess on how you can determine the “value”? That’s right, the free market society with live in allows for pricing to be a considerable indicator as to what you’re getting. Just decide if you want lodging, good food prepared for you and the type of guide service you want to have at your disposal. Most places will either take you to a stand or tell you exactly where to go. People don’t actually sit in blinds with you all day long unless you’re a celebrity of some sort traveling with a camera crew.
Step #3: Book your Kentucky deer hunt! If you’re wanting to gun hunt you better book 6 months in advance. Most are sold out within a few months of Kentucky deer hunting season.