I don't have any information on any of the names you list, but I also have a Scaggs/Naylor connection in DC. My grandfather, Charles Edward Naylor, married Fannie Helen Scaggs - don't have the date yet.
George was the son of Franklin Pierce Naylor. He was born abt 1882/1884 in DC and died abt 1939, also in DC.
Fannie was the daughter (possibly adopted or step-daughter) of Eugene Scaggs. She was born abt 1888 in DC and died abt 1958-60 in Palmer Park, Maryland.
Family lore has it that Fannie was the daughter of Fannie Pearl UNK, born abt 1865 in England and that she died aft 1943 in DC. Fannie Pearl may have been married to a Vanderlehr (or Venderlehl) before she was married to Eugene Scaggs, and that her daughter, Fannie, was the product of that union. Since I can't find much (anything!) on Vanderlehr (or Venderlehr), I haven't been able to resolve this puzzle. Fannie Helen is listed in the 1920 US Census as the daughter of Eugene Scaggs. It may be she was Scaggs daughter and the family lore is incorrect. It is still an interesting mystery and I am looking for a breakthrough.
Since we both have a Scaggs/Naylor union, we should keep in touch in case our trees cross. Problem is that there are a lot of Naylor's and more than one Naylor tree.