Here's a boat that went from Lake of the Ozarks to FL. It had to be hauled to the Missouri river first. You can get to Chicago once you get on the Missouri. What you buying? http://heartlandboating.com/special-delivery-from-lake-of-the-ozarks-to-florida-part-1/
You can not get to Lake of the Ozarks by water. You will have to truck or trailer at some point. A lot of the haulers will put in or take out in Alton Illinois.
Nope. You can have it hauled to/from the Missouri in Jeff City, but the entire trip can’t be done on the water.
Port Charles on the Mississippi is a common drop point from the Lake. Many Loopers stay in Grafton and Alton Marina. Both are 5 Star marinas.
Never stayed at the Grafton marina, but my parents were members of Alton. Definitely a great place. Can’t say enough good things.