I think this is a good plan. Like you said, the officers and adjutants were pretty good a mileages.
As for the known geographical points: We know (with reasonable certainty) the locations of North Fork Town (enudated by Lake Eufaula), Old Fort Holmes, Wapanuka Academy, Texas Road crossing of Middle Boggy, Geary's Station (Atoka Reservior), Ft Washita, Ft Arbuckle, Boggy Depot, and maybe Gov. Winchester Colbert's house/mill.
I believe I posted some time back what I had collected regarding the different encampments in the area and the different names used for the streams/rivers in the area. There were camps on Little Boggy, Middle Boggy, and Boggy (or South Boggy) and at Boggy Depot. The camps on Little Boggy and Middle Boggy watched the Texas Road and the Ft Smith-Boggy Depot Road and apparently had good water and grazing.
The Chronicles article about Old Stonewall is why I believed Cochran's is on Clear Boggy (aka South Boggy or just Boggy). There is a cemetery there with Cochran's buried in it. Seems Danny Knight has some connection with this family, if I remember right, and has posted about the Cochran's before.
However, I've never seen a map that showed Cochran's or Cochran's Academy or just Academy on the Clear Boggy south of present Frisco. The old maps all show Cochran's in the Choctaw Nation on or near Middle Boggy.
I'm still struggling with whether Cochran's was on Middle Boggy as shown on the maps or on Clear Boggy south of Frisco. I've speculated that if the maps are wrong but Phillips knew he was a Cochran's, he would have thought he was in the Choctaw Nation on Middle Boggy instead of in the Chickasaw Nation on Clear Boggy.