Hi Jackson, I don't know if you are still watching this thread, but a letter written by your great grandfather to the asylum that sent him to Illinois was published in 1884. Please check out my website where I am researching the orphans sent to Illinois by the New York Juvenile Asylum. He also published a little of his story in the some Chicago papers. I am writing a blog post about him and will have clippings from those papers in the post.
My website is http://rochellegridley.wixsite.com/orphantrainmap