1)Currently it is against a KAR, or a KY regulation to carry at the state fair. Gutshot and myself are working on reversing that regulation. Unfortunately, Ritchie Farmer is a stumbling block in this matter. Everyone vote 'Comer' for Ag Commissioner!
2)Definitely OC at court days--I will be! No need for zip tying your weapon. I might recommend carrying unloaded if you are looking to sell or trade it.
3)If you don't have a CCDW, I would not recommend carrying in that way in a vehicle. People here will tell you all day long that it is legal to do so. Personally, I believe the gun is mostly concealed when on the belt and sitting down in a car. Your call.
4)Don't get caught up so much in whether a place is OC friendly or not. The worst that could happen is educating someone on OC or being asked to leave somewhere. You won't be arrested. While OC is not commonplace in Lexington or elsewhere, it IS commonplace for several of us to OC in these places. We regularly have good or non-experiences. It may be unnerving at first, but that will change.