I might be able to help you regarding Will Freeman. He mostly rode with Albert Cunningham, who was a lieutenant with Quantrill. According to John Edwards (in his book about Gen Shelby) says: "On Big Creek, Cass Co in Dec of 1862, when the camp was surprised by the Feds, and killed one of his splendid soldiers, Will Freeman, and drove the rest of the Guerrillas back into Jackson County." Not sure if Edwards is right about the date. This would mean that Will stayed behind when the rest of the guerrillas went to Arkansas. Cole Younger (who also had a group of men with him that stayed behind) was another who stayed in MO to watch over his family. Most of the men that stayed that winter stayed for that reason.