[3] He established himself as an architect and superintendent in room 8 of the Townsend Block, located at the corner of Main and Swan Streets in Buffalo, in April 1879[4][5] and relocated to Minneapolis, Minnesota from 1882 to 1885, during which time was a partner (separately) with John L. Telford [6] and O.P.

In 1878 Caulklins married Jennie Louise Van Slyke (1858–1904) of Rochester, New York,[5] with whom he had a son and a daughter.

[8] He moved to Missouri in 1903, became a widower in 1904 and then married Gertrude B. Smith (1880-1938), with whom he had two more sons and another daughter before they were divorced.

[10] Between 1876 and 1881 Louise Blanchard Bethune, one of few female professional architects at the time, worked in his office and for Richard A.

[11] Other projects included a remodel of the Linwood Avenue house on the southeast corner of Linwood and West Ferry; design of the building at 410 Delaware Ave. (demolished in 1966); 430 Delaware Avenue building for Thomas Ramsdell; building at 85 Genesee Street (demolished); State National Bank at 8 Webster Street in North Tonawanda; and the 1888 Maple Street Baptist Mission Church (demolished early 1980s).