My opinion is that this game (and Monkey 1 and Monkey 2) are entirely allegorical. It is not a literal pirate adventure, and taking it as such will inevitably lead to disappointment.
RtMI (and especially the ending) cements for me that the series is intended to be allegorical.
This is more or less explicitly confirmed by Ron and Dave in the addendum to the scrapbook.
The Chum quest in particular seems to get at the heart of the secret: people want to feel what you felt at some exciting point in your life, through the use of grandiosity and colorful fluff. Monkey Island was the creators' fluffed up story of their lives and how they look back on their adventures as explorers of uncharted territory
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Posted · Edited by Jake2JakesRevenge
This is more or less explicitly confirmed by Ron and Dave in the addendum to the scrapbook.
The Chum quest in particular seems to get at the heart of the secret: people want to feel what you felt at some exciting point in your life, through the use of grandiosity and colorful fluff. Monkey Island was the creators' fluffed up story of their lives and how they look back on their adventures as explorers of uncharted territory