My BrickWall

2. Is finding Thomas H. Singleton in Baltimore City between 1916 - 1929
and finding his father, Charles Neal.

Have you tried Baltimore City Directories and/or AA Newspapers for that area during the 1916-1929 time period?

Is this your Thomas Singleton enumerated in the 1930 census? This Thomas Singleton is listed as a 30 y/o Teacher in a Public School with a 2 y/o son also named Thomas Singleton. Address shown as 1137 Bolton (?) Street.

1930 United States Federal Census about Thomas Singleton on Ancestry.com
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Name: Thomas Singleton
Gender: Male
Birth Year: abt 1900
Birthplace: Maryland
Race: Negro (Black)
[Black]
Home in 1930: Baltimore, Baltimore (Independent City), Maryland
Marital Status: Married
Relation to Head of House: Head
Spouse's Name: Sarah Singleton
Father's Birthplace: Maryland
Mother's Birthplace: Maryland
Household Members:
Name Age
Thomas Singleton 30
Sarah Singleton 23
Geraldine Singleton 7
Horace Singleton 5
Mary Singleton 3
Thomas Singleton 2
Rosa Le Fato 60
Annie Harrington 52

La Fato & Harrington are enumerated as Lodger's in the Singleton household.