The source of the information on the earliest history of Osceola was the 1880's county history that John Lapsley Mills showed me in the town library. It was that history that described the earliest inhabitants as including the white, or mostly white parts of families who had been split up when the Cherokees were mostly forced west of the Mississippi into what is now Oklahoma. The writer had interviewed children and grandchildren of the first settlers of the town. Remember, these were mostly white or white, though. Their less white kin were in Oklahoma.
There were some Collins lines in this area, though that connect back to Collins who were indeed a quarter or more Cherokee and whose parents were literally indicated as "Indian" on the early census and county records in Kentucky. They kept losing land because of their race and sometimes tried to fight for it. You'll find a lot of Cherokee in the early 1800's in Floyd and Clay Counties in Kentucky--and they are quite well documented. I descend from the Sizemores of Clay County--a family that was well documented to be Cherokee and mostly descended from a renegade war chief named Red Bird. You can still find a nice Wall Street Journal article about this family, its history and its notoriety even today. Also some of the Lemar/Lamar family was part Cherokee. The first wife of William Lemar/Lemarr, etc. of Botetourt County, VA was Cherokee and the three or so children of that marriage have been found to be listed in records as "half-Indian." One brother of William Lemar Jr. (full brother) of Anderson County, TN, went west on the Trail of Tears. William Lemar/Lemarr Sr.'s second wife was white, however, and the half brothers and sisters of William Jr. are listed as white. I also descend from William Lemar Jr.