Have you sketched out the migration of your ancestor on a map? To help sift out two men with a similar name, I put all their pre-1850 census enumerations on a map of New York, marking the locations. Sometimes a picture helps.
I was recently helping a friend with a genealogy problem and all our discussion appeared in a chat window in Facebook. I kept thinking to myself that I would have been less confused if I could have had the information in some sort of chart or chronology and another sheet with locations mapped out.