A stock JTR would be fine for certain trails in the DBBB in normal conditions.
As mentioned above, Spaas Creek is notorious for being difficult in wet conditions. But most of Fixer-Leeco Rd is fairly easy.
I go by myself most of the time. If I run into difficulty, I turn around. I don't have...
Several Facebook Groups for Kentucky Off Roading, but I don't know any specific ones for Jeeps. People are constantly going to the Daniel Boone Backcountry Byway. I'll be there Saturday.
I go to the DBBB a couple of times a year. It's a good place when relatively dry. When it's wet you don't want to go alone and you definitely want recovery gear. There is a map for it at:
https://www.cartotracks.com/daniel_boone_backcountry_byway
Carl was mine as well. Great guy.
I'm having mine serviced there. My fiancé has a Jeep Wrangler and they have done good work on hers. They have two extremely knowledgeable Jeep guys that love to work on them.