In the mid-1890s, Edwin became head of the Florida Coast Line Canal and Transportation Company and then the Model Land Company, both of which sold land for the railroads. In 1900, after twenty years living in Lake Worth, the family moved to Flamingo in Monroe County, near the Everglades. Edwin had heard that railroad tycoon Henry Flagler planned to build his railroad through the area, and that the then primitive city of Flamingo would flourish as a result; Flagler later changed his mind, deciding to build to Key West instead. Guy and his brother, who continued working as guides and hunters, each received a quarter of a mile of land on Florida Bay as part of their father's deal with the Model Land Company. While working variously as a postman, farmer and boatman during his 20s, Guy continued to augment his income with an occasional plume hunt. In 1899, he married the young widow Sophronia ("Fronie") Vickers Kirvin from Key West. Their first child, Morrell, was born a year later.