I found Sylvester Bailey in the Border Crossing from U. S. to Canada 1908 - 1935. On August 31, 1933 he was in Fort Erie Ontario. He Listed his name as Sylvester H. Bailey of Rice, Virginia, age 44, Married, Baptist, Wife-Christine Bailey. He had 22.00 dollars on his person when he crossed the border. I believe he was crossing the border for business. tobacco curers. He also named Employer as Melvin Horton Courtland.
In the 1930 census I found Sylvester Bailey living in Prince Edward County, Virginia. His wife was Christine He had five children, Elsie B 13; Lawrence Bailey 11; Louise E 10; Raymond B 7; and Ela 4 1/2.
The Social Security Index has Sylvester Bailey departing this life in November, 1968.
So to summarize my findings for Sylvester Bailey.
He was born in Pittsylvania County, Virginia to Robert L. Bailey and Henrietta Bailey on November 3, 1888. He was still at home with his parents in 1910 at the age of 21. Sometime between 1910 and 1916 he was married to Christine. I do not have her maiden name. I could not find a 1920 census. However, in 1930, he is listed in the census as living in Prince Edward County Virginia as a farmer with Christine and five children. It also states that he was not a verteran. In 1933, we see him traveling to Fort Erie Ontario for Tobacco business.
In November, 1968, he dies and the Death Index has him still living in Prince Edward County, Virginia.