The second letter (from "Lorraine" to your grandmother) below is a puzzler. The topic of the letter is Lavery genealogy, with margin annotations which at first glance, appear to have been made by Helen. There are two distinct handwriting types on the letter. Maybe notes on the family that Helen is leaving behind for Arden? One in particular stands out: "My mother's father Wm D Lavery a brute my mother hated him". (Helen was beginning her descent into dementia at this point, and was not always remembering things clearly -- it could well be an erroneous memory. Lorraine says that her mother had fond memories of "Old Bill," but acknowledges that Ella and Helen did not share those fond memories.) This letter is mined with clues; I just hope we can make sense of them. Click to biggify:
At the bottom, Lorraine is musing on Wm Lavery's whereabouts between Nov 1862 and Mar 1863. Click here for more info on the 44th NY Infantry's involvement in the Civil War. UPDATE: I just received Wm. Lavery's entire Civil War Pension File, which described that he was gravely injured in the second battle of Bull Run at the end of August, 1962. His leg was eventually amputated (when he was about 50 y.o.) due to that injury. Subsequent to finding this letter, I was extremely lucky to be able to make contact with Lorraine through Ancestry.com. She had a ton of information on the Lavery family, including photos!
Also in this stash was a postcard album, with postcards dated from 1905 - 1912. It provided addresses for your grandmother and great grandparents in Chicago and Alameda for that time period. A couple of the postcards were incredibly politically incorrect, but typical of the time. I'll try to scan them this weekend.