Tattered Sunshine comes for a visit

Tattered Sunshine 1894 Nelly Kennedy

The painting here, Tattered Sunshine, is a precious memento of my mother's grandmother, Nellie Kennedy. My sister and I share him, and for a while it's my turn. He will eventually go to my niece. Nellie signed the painting and dated it, but the date is difficult to read. It might be 1894.
We know very little about Nellie Kennedy. She married a Daniel Aloysius Gillin who was appointed to the rank Cadet of the United States Military Academy 1893. I've found on-line records of a Daniel Aloysius Gillin who worked in the Government Printing Office during the 1908-1912 period. They lived on A Street NE on the fringes of Capitol Hill. Nellie had time to paint, and her brother who lived with her ( my mom called him Unc and he was a favorite) played the guitar. A picture exists of Unc sitting on the front porch of the home (walk through that neighborhood and you'll see many like it) holding a guitar. There's a family story that Unc had a girlfriend he visited every Wednesday.
Did Daniel Aloysius graduate from West Point? So far, I have not been able to discover that. He might have died about 1920 because that seems to have been  about when Nellie and the daughters moved back to Philadelphia. It's all mostly guesswork on my part.
Update, February 3, 2017: evidently Daniel did graduate from West Point - we've found a telegram addressed to him in which he is requested to return tickets to an affair sponsored by his West Point class because the president needed the tickets. POTUS or president of his class - I'm not sure yet.