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I'm sorry, but I don't find any earlier connections between the DAUGHTRY and KIRKLAND families. I assumed that Guilford was a hired hand, just as "Lousa BOLTEN" age 25 was a housekeeper, the same Louisa BOLIN age 16 who was a servant in Decatur in 1850. Be aware that Guilford is indexed 1860 as "Galford RICKLOINE," and that many of the KIRKLAND entries in western FL are misreadings of STRICKLAND, another allied family.
The DAUGHTRY family had connections in Grady and Thomas counties GA, as well as a stretch of FL counties from Walton to Suwannee. A man named Guilford KIRKLAND received a homestead in Suwannee in 1896, but I doubt that he's the same individual.
My hunch would be that you should pay particular attention to the family of Moses and William STRICKLAND, b. 1791/1799 in SC, who migrated in Walton Co. FL, leaving descendants along their path. You should also be able to work backward from Annie Iola KIRKLAND; I'll send you direct the names of researchers who know more about Robert Cleveland BRASWELL.
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