Great article; I completely understand what you are saying about the game affecting eleven year olds’ worldviews — because I was one of those young ones infiltrating the age requirement quiz.
If I recall correctly the final “win screen” (spoilers ahead) occurs after you (Larry) have found your true love in the casino penthouse hot tub. The parade of LLL sequels notwithstanding, it seemed to me as a naive pre-pubescent that Larry succeeded in leaving his sordid past behind in favor of a more favorable (or at least less socially frowned upon) relationship. Yet, it was a relationship built on deception and larceny, (the aforementioned diamond ring!) In looking back after reading your post, I suspect it was all a massive inside joke being played upon us (underaged players) by the Sierra game developers — with my dad who purchased the game chuckling right along.
To this day, I refer to going to the restroom as having a “sit and think”.