Kentucky IS very strange in how it identifies itself. Part of this is because it fought for the Union but was split idealogically, often within families... and so it's been ever since. It's considered a "southern" state but has a sizeable portion that is geographically further north than parts of Ohio (including Cincinnati) and Illinois. "Bootstrap of the North and Top Hat of the South" is a phrase I've heard, and it fits.
But nevermind its place within country: it suffers identity crises within its own borders. The schizophrenic panic that Lexintonians go into if you consider that town part of "Eastern" (and not "Central") is hilarious, even though it is clearly situated in the eastern third of the state.
Apparently the name "Kentucky" means "Land of Tomorrow" but it's become more dated than a Disney park. Parts of this state - such as where my in-laws live - look like they've hardly changed since 1958. Which is kinda awesome on one hand and horrifying on the other. People continually vote and act against their own self-interests. Our one stubborn senator continues to ride on the coattails of an auto plant he got built 30 flipping years ago - what has he done for anyone since? And yet he's got them convinced: the interviews with Obamacare beneficiaries who admitted to being significantly better off with it, but were going to vote against it because, well, *you know*... were so facepalmingly alarming that the election was not a surprise. In 2009 I installed IT infrastructure in functioning, permanent, public facing country courthouse building that that did not have plumbing. The clerks had to go to another building across the street. In 2009!!! I think that was finally renovated in 2010? At least I hope so before the Ark Park was funded...
So yeah, Kentucky is backward where it's awkward and forward where it's alarming.
And yet it's beautiful with well-preserved wilderness, and plentiful, gorgeous state parks. Driving roads like you wouldn't believe for the central continent. Affordable if you make a decent wage (we're the canary in the coal mine for the race to the bottom, but won't admit it) - if you retire here with mad bank you could live like a king. Louisville hasn't forgotten its gritty side and has lots of character. Lots to like, lots to roll your eyes at, but good enough for me to stick around for 18 years and counting so who am I to complain?
(At least its not (yet?) totally morally and financially bankrupt like the godforsaken state I fled! )