From everything you've listed--this sounds like a fit to my family.
Frances Leonore Walden--- Walden was her maiden name. There are a lot of different stories about why she never married and why the three boys all bear her maiden name. One of the stories speculates that a John Thomas "Don" was the father of at least Gilbert. Frances was said to have been born Oct 6, 1877 in Clark County, Mississippi. She died Jan 29, 1949 in Bay Springs, Smith Co., MS. She supposedly lived most of her adult life in Vicksburg but later moved to Lake with Gilbert and his family. I believe I found Gilbert and Mark in the 1910 census at Devereaux Orphan Asylum, Natchez City, Adams County, Mississippi.
Gilbert married Florence Mapp Aug 2, 1922 in Newton Co., MS. In the 1930 census he and his family are found in Beat 4, Newton Co. Their children are Mark (1923-1990), Frances E. (1925--my grandma-2000), Gilbert Joseph (1927-1930), Thomas Elton (1929-1929), Milton Lee (1930-), Mary Leona (1932-1932), Lola Agnes (1933-1990), Charles Edwin (1935-1995), Nolan Doyle (1937-1937), Gerleine (1939-), Joan Mignonne (Nonnie) (1941-), and Deloris (1943-1943). The family had their share of hard times. It's possible that the Gilbert A. Waldron isn't the same Gilbert or he may have been in Vicksburg trying to earn some money when the crops may not have been so good.
This Walden line goes back from Frances "Fannie" to her parents: Thomas Byrd and Celia Jane. Thomas Byrd's parents were Tillery David and Mary Felisa (Jones) from South Carolina. This is far back as I am able to go so far. I've not heard of a Chaney Bobo Walden--but doesn't mean he isn't related to one of Tillery's possible siblings. I live in Colorado and don't have a lot of opportunity to travel south since my grandma passed away. I do hope to make a trip down to do some research in the next couple of years.
Let me know if you are interested in anything else on this family--or tell me about Chaney and I'll see if I can find where he might fit in. Feel free to contact me directly at email@example.com