Thanks for the help, I'll review the data in Cavaliers. It is my understanding that Thomas Keene was free as a landowning gentleman, but there is also the possibility that he was in debt for a portion of years. Perhaps a person could pay for some portion and work for another portion. I do think that there was only one Thomas Keene during this time frame between 1630-1640 in the Northern Neck area, no matter how it is spelled. From my understanding, both Clayborne and Capt Evelyn have connections to Thomas Keene in 1637/38 records.
Remember the curious circumstances of Anthony Gosnold (the younger one, son of Robert Gosnold IV and Amy Forth) who arrived with the Virginia company in 1607 and lived through 'the starving time', who was forced into 16 years of servitude when he should have been as free, when he felt he should receive the land portions of himself and his two kinsmen (perhaps meaning his father's 1st cousins, Bartholomew and Anthony Gosnold, sons of Anthony Gosnold and Dorothy Bacon). This Anthony, complained about the unfair treatment of the Virginia company and even after finally receiving two portions, one for his payment, one for his services, he was made to prove his case in front of the Virginia governor. According to my understanding, Anthony returned to England and married, giving his portions of land away, one to his brother Robert and to Roger Castle (who is also family somehow).