There has been some mention on the GORC message board of the new Ozark Trail Shuttle operated by the OTA, and how convenient and useful it is for doing point-to-point rides which had previously required you to go through the hassle of arranging vehicles for drop-offs and pickups.
What hasn't been talked about much is a new way for you to explore the Ozark Trail, and perhaps ride some sections that you may have never thought about riding, or even heard about before, for that matter. This is the trip planner. Here are a few screenshots which show how you can choose the type and length of ride you wish to do from a particular trailhead. It then gives you the options available which meet your criteria and gives you links to the relevant topographic and GORC-style area maps, as well as very detailed directions which will make it very difficult to get lost. You can then see if a shuttle is available for the date you wish to go, and if not, perhaps arrange for a custom shuttle.
This is a fantastic service that is the result of the settlement by AmerenUE over the Taum Sauk Reservoir incident. It's also a great way to find out more about the gem of a trail that we've got in our own backyard.