I did lots of hiking/backpacking along the OT back in 2001-2003 when I lived in the St. Louis area. I've added a few pictures. If you haven't yet you should review the three mountain pages I have added for Missouri. I think the OT passes near all three of them.
Feel free to link to them if you like.
Thanks, and I've set up those MO mountains as "related pages." I'd love to see more -- perhaps you have more ideas in your pocket?