Leonard, b. 1896, was separated from his family following his mother's death in Kansas City, MO in 1904. He lived with his maternal aunt and uncle in Maine. He returned to Kansas City, but no one seemed to know exactly when. His father and eldest brother had left Kansas City; I found them in the census records living in Topeka, KS. I haven't been able to determine who took the sisters, Pansy b. 1888 and Ida b. 1894. in to their home following the death of their mother.
One item I really wanted to find was his probate. Leonard died in 1965 having out lived his wife, Ethel, by four years. In the index was a probate case for Leonard L. Gregory but not in 1965 or any where near that year. It was filed in 1913 in Jackson County, MO. This was the first time I found evidence of his return to Kansas City prior to his first marriage in 1916. This "probate" turned out to be a guardianship.
I learned three things: he was back in KC by 1913, he found his sister Pansy (now Branscum) and he was under age when he joined the Army and needed parental permission. We also now know that he did not reunite with his father until perhaps after his service.
I was able to track Leonard and his family through the City Directories housed by the Midwest Genealogy Library following his military career. Beginning in 1915 he resided at 923 E. 9th in Kansas City, MO. Living with him is his father, Lewis L. Gregory. Leonard was a cook and Lewis a plasterer. Lewis was always a plasterer from what I have found in the census records and city directories. Leonard wasn't married at this time, no female is listed in the directory. He married Ethel in 1916. Leonard stayed in Kansas City, MO the rest of his life. I have tracked his siblings through the Jackson County Marriage records and the Federal Census records.
If you have family from the KC area, I recommend stopping in to do some research at the Midwest Genealogy Library. You never know what surprises you might find!