The key to winning Kentucky in 2016 would be to not only rack up good margins in Lexington/Louisville (Obama actually overperformed here in 2008 and 2012 for a Democrat), but to do well enough in coal country. Combining Gore/Kerry margins in rural Kentucky with Obama margins in urban Kentucky (he also did fairly well in the parts bordering Illinois and Indiana) probably makes it a Lean R state.
She wouldn't be able to rack up those urban numbers because she wouldn't be able to get that kind of turnout with blacks like Obama was able to.