Unless I'm missing something, not having those two mountain regions is costing me half the state, i.e., the American flag symbol is shown only for the top 'button'. The bottom button is grey (the AI hasn't moved into those regions either.
What regions are they? Not to offend, you might be missing something.
Rule 15.2 states you only have to control regions in Kentucky that contain population centers. All population centers in Kentucky are either on railroads or roads, so you should not have problems moving into them.
Most population centers all in areas of the game map contain roads (except northwest west Texas, southwest Missouri and maybe another random one I don't recall).
"L'audace, l'audace, toujours l'audace."