On May 14, 1911, he married Lucy McKeown of Quincy, Florida and they had two daughters. In 1913 they moved to Arcadia, where he worked for the Consolidated Title Company until 1921 when Hardee County was created. He then formed the Consolidated Abstract Company for DeSoto County and the McLeod Abstract Company for Hardee County. What was named the “McLeod System” was adopted by abstract title companies throughout the State of Florida. In 1923, the McLeods moved to Everglades, where he operated an abstract title company and began lifelong service to Collier County.
In 1923, Florida Governor Carey A. Hardee appointed Dan McLeod first Tax Assessor of Collier County, a position he held until 1960. He was Vice-President of the Bank of Everglades until 1960, Secretary of the Collier County Title Company, President of the Board of Elders of the Everglades Community Church, which he helped organize in 1926, Superintendent of the Sunday School, a member of the Collier County Board of Public Instruction, and a board member of the Deep Lake Grove Company.
He became the first editor and publisher of The Collier County News, serving in that capacity from 1923 until 1925. In 1927, Mayor McLeod was appointed first chairman of the Collier County Chapter of the American Red Cross, a position he held through World War II. He also served on the Selective Service Board and was a Government Appeal Agent.