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In southern Indiana we really get the crappy side of seasons on both sides.
Even though we are far north of the Gulf, it is the main driver of the weather here. So in the summer it is plenty humid. Nothing to be 90 degrees with a dewpoint 70 or above. It's like hot soup.
Winters are wildly all over the place here. We will often get a 70 degree day in December...but within 24 hrs it could be in the teens with freezing rain.
The best time here is the fall, but it is painfully brief. We have legendary fall weather here, with people visiting parks here from all over the U.S. In September we can have low humidity, breezy 70 degree days down in the 50's at night for the entire month and into October. So we may only get 30-40 really nice weather days a year.
When I retire, I am absolutely moving elsewhere...just not sure where.
What you describe is very similar to Kansas. We moved from there 30+ years ago. We still miss it, and I bet you'll miss Indiana too if you leave.