Paint Shop Pro came out in 1990, so you could do basic editing, however you had to find the Raccoon. Perhaps copy it from your Encarta CD, after you waited until 1993!
The main maps I used for driving (back in the day, UK, 1986) were 'books' rather than large fold out maps. At local level, an A to Z. At national level, an AA road map, this has the format of a small newspaper, however in thicker paper.
He's alive, so unlikely