I guess it depends on what part of Eastern Kentucky are you coming from. If you're coming from Corbin or Middlesboro (southern KY), you should be able to make Valdosta with no problem. However, if you're coming from Ashland (northeastern KY), you'd be hard-pressed to make Macon.
When we drove to Disney in January, we had to adjust our plans going down due to a pending snowstorm through Tennessee. We ended up leaving a day early and drove to just south of Atlanta. Even though we could have made it to Disney on the second day, our ressies weren't until day 3, so we drove to Tarpon Springs on the Gulf Coast. I'm assuming you don't want to do that.
Coming home we stayed just north of Atlanta (left about 6:30 AM). Unfortunately, can't remember where we stayed.
Can't remember too much about the restaurants along the route either. However, the rest areas were good and clean. I highly recommend spending time at the Florida Welcome Center. The free orange juice is a tradition stemming back from my first visit to Florida nearly 50 years ago.