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IMO, Kentucky should start the war with a grey border and no volunteers. Then change to blue (Union) if the CSA enters the state first, or red (Confederate) if the USA enters first, giving full support and troops to whichever side they join. Historically they demanded neutrality, and told both sides that they'd side against the first force to enter the state.
Edit; Just to note I don't play as the CSA often, if ever.
I do remember, at least in vanilla which I haven't played in a long time, that flipping Kentucky was easier if you did it very early on, sometimes before the north even had an army of any sort in the state, you could take Louisville as soon as readiness allowed and the state would join the CSA.
I've flipped both several times as CSA.
I know Kentucky has a second city, not sure about Missouri.