When I considered taking a hunting trip overseas it certainly was a daunting task! TRUST was the most important thing to me. They wanted me to send money to "this person" so it could be funnelled to "that person" who lives in Southern Africa. Everybody I talked to seem to be comfortable with the process. The outfitters and booking agent acted like this was normal and seemed quite trustworthy. My point is these professional hunters and profession hunting outfitters knew what they were doing and our trip went smooth! I know what it's like to call all these Kentucky outfitters trying to decide who to trust with your hard-earned money.
The fact is, and my main tip would be, if a Kentucky hunting outfitter can show you his home, his lodge or some valuable perminant structure like a cabin they own, then you at least know they are not a fly-by-night outfitter who just leases land from granny and then leases it to you an 25 others. Worse yet, they aren't doing a Kentucky hunting lease from anyone and they are just saying they have land...taking your money and never to be heard from again.
Another tip would be to make sure Kentucky deer hunting outfitters have a website. It's a sign of stability. All these indicators add up to a place you know at least you're going to get to hunt. Kentucky hunting forums can offer good leads and recommendations, but I warn you about "google reviews" and people who bash others. The reality is deer hunters are not those who sit in mommy's basement being a social justice warrior curled up in the feetle position needed their safe space. Kentucky deer hunting has quality people involved. If someone is bashing a Kentucky outfitter, I believe it was an isolated incident of unfortunate events, which 100% of the time I'd bet they didn't shoot a buck as well.
I know a company who I feel is the biggest in Kentucky. He's the only one I've seen talk down to other Kentucky outfitters and I've seen many bad reviews...but the fact is Wal-Mart has many bad reviews. Anyone who might be the biggest and best will also likely have the most bad reviews. This is me coming in defense of these types of folks. Use common sense and understand people have bad experiences all the time. I'd estimate the value of a Kentucky trophy deer to have an average worth of $6,000. It's probably more, but Im not really factoring in people like me who some spend $50,000 per year to hunt their own property. People buy expensive land to only hunt...therefore, you need to calculate the value of that high price because they are spending that much money in hopes of shooting a trophy buck.
Read the Kentucky hunting forums and learn as much as you can. Take everything with a grain of salt and use your best judgement.