I don't have any info to help you but I also am fascinated in topic. I know that my ancestors, per an 1869 obit, took some of the same route as you mention: VA, KY, MO, TN, AR, TX, MS and in locating some of the places I've noticed that most--for two families who married into one another--followed closely to the Mississippi River at first. Don't know what they did, other than one was in 1848 War with Mexico in TX, then in Civil War in MS/LA and that his sister married on MS River in Helena, AR. The trading is interesting!