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Are you going to be working your way up to this century? I just kind of wondered how many rounds you're thinking of. I'm really enjoying this out of the ordinary congrats! :)

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LadyBug

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Clare gets married in 1980. Jeffery gets married in 1976. Esther and Franklin welcome a daughter in 1977. Theodore and Ruby welcome a daughter in 1979. Geraldine and Matthew welcome a son in 1978. Clyde gets married in 1976 and welcomes a son with his wife in 1979. Anna gets married in 1978.

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DH: Lawrence Walter (1880)
DW: Edith Cordelia (1881)

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DS: Oliver Sidney (1902)
-DW: Marjorie Flora (1901)
--DD: Ellen Mabel (1923)
---DH: Roland Douglas (1922)
----DS: Gordon Calvin (1951)
-----DW: Angela Marlene (1954)
----DS: Clarence Matthew "Clare" (1955)
-----DW: Charlotte Rosa (1955)
--DS: Gilbert Ronald (1925)
---DW: Lucy Genevieve (1925)
----DS: Jeffery Benjamin (1953)
-----DW: Emma June (1951)
----DS: Joel Bradley (1957)
--DS: Wallace Bruce (1929)
---DW: Vera Loretta (1930)
----DS: Mitchell Duane (1956)

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DS: Gerald Hugh (1905)
-DW: Maude Emily (1906)
--DS: Curtis Oscar (1930)
---DW: Janice Roberta (1931)
----DD: Wendy Suzanne (1957)
----DD: Elaine Frances (1958)
----DS: Jack Frederick (1965)
--DD: Ida Jeanette (1932)
---DH: Keith Alan (1931)
--DS: Phillip Cecil (1935)
---DW: Elsie Marian (1935)
----DS: Adam Eugene (1964)
----DS: Brent Albert (1968)
--DD: Laura Bernice (1938)

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DS: Earnest Horace (1909)
-DW: Sadie Estelle (1909)
--DS: Jesse Victor (1936)
---DW: Annette Lucille (1938)
----DD: Melinda Jane (1966)
----DD: Alicia Danielle (1969)
--DD: Esther Constance (1938)
---DH: Franklin Lewis (1939)
----DD: Alison Monique (1977)
--DD: Priscilla Christine (1940)
---DH: Leo Warren (1940)
----DD: Yolanda Rachel (1967)

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DD: Ada Kathleen (1914)
-DH: Nicholas Luther (1917)
--DD: Lillian Cynthia (1941)
--DS: Theodore Edwin (1947)
---DW: Ruby Charlene (1946)
----DS: Henry Alexander (1972)
----DD: Aimee Katrina (1975)
----DD: Jillian Natasha (1979)
--DD: Geraldine Rosemary (1950)
---DH: Matthew Randolph (1950)
----DS: Seth Roger (1978)

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DD: Harriet Eileen (1917)
-DH: Leslie Irving (1917)
--DS: Clyde Bernard (1949)
---DW: Laurie Marianne (1950)
----DS: Martin Trevor (1979)
--DD: Anna Evelyn (1954)
---DH: Charlie Terrence (1952)