I worked with a guy who Leisure Suit Larry was based off of, appearance wise. His name was Nick Medici (sp?) and he actually was a really nice, gracious guy, but looked exactly like LSL. He told us stories of the Sierra days and the husband/wife that ran it. He also cooked really tasty food for us!
I recently read a book about ocean-crossing by private boat that turned out to be written by Ken Williams, the cofounder of Sierra (i.e. the husband you mentioned). It turns out that being ultra-rich from founding and selling a major software company can open doors to cool, expensive hobbies.