Married to Daisy Lee Covert, daughter of Richard Archibald Covert and Mary Ellen Patterson, on November 26, 1902 in Chicago, Illinois. Jim was father to Virginia May (m.d Charles Wilton Kearnes), Lorraine Elizabeth (m. Charles William Upton), Earl Covert Wayland (m. Marguerite Mariel "Peggy" Wood).

When Jim went to Roanoke, he laid track for the street cars for Roanoke Street Railway Company. He realized his job was near completion and he would be out of work. Jim figured someone would have to drive the streetcars, so he went to the main office and asked for a job as a motorman. As he was 18 at the time, and the age requirement was 21, he didn't get the job. But John tried again, avoided telling his age and got the job, being one of the first street car drivers, called motormen, in Roanoke. This would have been around 1895.

At the election of officers on January 5, 1896, Jim was named "Outside Sentinal" for the Roanoke Council, No 70, Jr. Order of United American Mechanics.

Jim was the first in the family to move to Chicago to live. As many of his family members were electricians, it's likely he looked for that type of employment.

Jim's brother John, and his cousin, Marvin Wayland from New Franklin, Missouri, lived with Jim's family in Chicago in 1900. All three were listed as mechanics for the railroad, which were likely electrician jobs. His father-in-law worked for the same railroad.

By 1910, Jim was an electrician journey man. In 1918, Jim worked for Henry Newgard & Company (Electrical Engineering Company). In 1920 he was an electrician in construction and in 1930, a shift electrician for a corn producer. Jim was a salesman for a wholesale food supply company in 1940. Per family information he worked for Argo Corn Starch Company as head electrician in the later part of his career.

By 1930, Jim and his family moved from 10828 South Western Avenue to 11249 Longwood Drive, Chicago, Cook County, Illinois where he and his wife lived the reminder of their lives. They did travel to their summer home in Momence, Illinois.

Jim lived relatively close to his brother John, who also had moved from their family home place in Madison to Roanoke, Virginia then on to Chicago, Illinois. His brother John was living with Jim, when John passed. There is a newspaper article in 1918, which inaccurately states Jim died at John's house, when in fact, it was the other way around. This can be confirmed by the addresses listed in the newspaper article and by John's death certificate.

Both he and his wife were active in the Chicago community. Jim died in Chicago, as did he wife, but the location of their graves is unknown at this time.

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Newspaper articles on family members:

1896 (14 July) ARRIVED IN ROANOKE. F. N. Wayland, father of J. E. Way land, mail carrier, and James A. Wayland, motorman, arrived in the city today from his home in Madison county, Va. Mr. Wayland and his son, J. E. Wayland, will leave to-day for New Franklin, Mo., to visit relatives for thirty days and will return by way of Chicago and take in the sights of that city. [Source: The Roanoke Times, Roanoke Virginia, 14 Jul 1896, page 5.]

1896 (13 Aug) J. H. Wayland and father returned yesterday from a month's visit to friends in Maryland. J. H. Wayland, of Chicago, formerly of the Roanoke Street Railway Company, arrived in the city yesterday

1896 (Aug) FAMILY REUNION. The Howard County (Mo.) Advertiser has the following: A family reunion was held at the residence of N. S. Wayland, at New Franklin Wednesday, three brothers and three sisters being present, together with their father, who is now in his 82nd year. The children present were: F. H. Wayland, of Brightwood, Va., J. W. Wayland, of Franklin; W. T. Wayland, of Fayette, and Mrs. Sarah E. Carter, of Saline County; Mrs. Annie Carpenter, and Miss Lucy Wayland, of New Franklin. The last reunion of the family was held at the old home place in Madison County, Virginia, on March 17, 1869. A large number of grandchildren and other relatives were present at the reunion Wednesday and it was a most joyous event for the family, though many faces were missed from the family circle, who has gone over to that other and better land. J E. Wayland, of the Roanoke post office, and J. H. Wayland, his brother, of Chicago, who is now visiting friends here, were In attendance.

1897 2 Oct DELIGHTFUL TROLLEY RIDE. A trolley party was given Thursday night by the young men of the Street Railway Company. Refreshments were served aboard the oar and the occasion was one of great enjoyment to all who participated. Among the young ladies in attendance were Miss Annie Deacon, of Lynchburg; Misses Mary, Rosa and Elsia Fuqua, Annie Brown, Minnie Pollard and Dowdy, of Vinton; Misses Fannie Wayland, Callio Smith, Ruth Dyer, Mao and Lizzie Bennett. Fannie Stiff, Mollie Hackler. Hattie Wingfield, Laurie Pollard, Ida Franklin. Mary Bannders, Hart and Moore, of Roanoke.

1926 Sept Mr. and Mrs. James A. Wayland, 11249 Longwood Drive, returned from their summer home at Momence, Illinois. [Suburbanite Economist, Chicago, Illinois, Tuesday, September 6, 1927, Page 5].