I had a friend from Illinois that shared Devil's Night stories with us.Where I came from, Detroit, not only was Halloween a big night but also Devil's Night the night before. Parents would even take their children out in groups up and down the block soaping windows and people played harmless pranks on each other. Over the years, it did really get out of hand and Detroit would look like a war zone on that night of the year.
I like your idea of a costume Skippyboo! Of course Uncle Harry would insist on getting in on the act there somewhere.