This kind of depth and humor should be expected from Winslow Homer and his Tile Club friends.
Many of Winslow Homer's friends were writers. There is considerable material that can provide a sense of Winslow Homer and his friends.
Read the works of Homer's Tile Club friends:
Tiler F. Hopkinson Smith The Wood Fire in No. 3. A meaning of the word "chestnut" has been preserved by Henry James, but came from Tiler Edwin Abbey. That story is in this book.
Tiler A. B. Frost is considered the father of the modern cartoon.
Read Tiler Elihu Vedder's Digressions of V. - Written For His Own Fun and That of His Friends.
Tiler Gustav Kobbe's Opera Guide is still being revised and republished as a definitive guide to opera.
Read Philip Beam's Winslow Homer at Prout's Neck to get a feel for Homer's character.
Read from The Century 1847-1946, a History of the Century Club, chapters which deal with Homer's time. The double images such as shown here are not out of character for Homer.