The update includes issues into the 21st century with the Newspapers.com Plus subscription, but I haven't found any close relatives much past the following 1918 find.
Since I am easily distracted into doing newspaper research, I decided to see what I could find by searching on Adsit, one of my more unusual ancestral surnames.
From The Courier-Journal, Friday, November 22, 1918, page 5, column 2:
Mrs. Charles Chapin Adsit and daughter, Miss Elizabeth Adsit, of Chicago, are spending the week-end at the Seelbach [Hotel], having come to see Mr. Charles Pyle, who is a candidate at the F. A. C. O. T. Miss Adsit's engagement to Mr. Pyle has been announced.
F. A. C. O. T. is The Field Artillery Central Officers Training School. Google Books provided me with the ability to read The Story of the Field Artillery Central Officers Training School, Camp Zachary Taylor, Kentucky by Raymond Walters (and others), published in 1919.
I had never heard of this school and certainly never knew that my grandfather attended it.
This school only existed from June 1918 to February 1919 and in November 1918, it had become the largest school in the world with 16,598 candidates and enlisted men participating. My grandfather, Charles M. Pyle, was graduated from it (though I don't know when); he is listed as one of the alumni on page 250, with his home address as the Hotel McAlpin in N Y City.
For those interested in learning more about F. A. C. O. T., I'll let you read the book yourselves.
Elizabeth Adsit and Charles Pyle married on March 1, 1919, in Chicago.