I know I’m late to this, but I think it’s an interesting area.
With regard to the CMI team’s perspective on MI2’s ambiguity: I always figured that literalizing its predecessor’s ending was more about making a judgment call not to disappoint what they perceived were the audience’s expectations (“What’s this soluble daydream hokum doing in my pirate game?”), rather than it necessarily representing a personal distaste or rejection of the innuendos Ron was making.
Skirting that stuff may have in fact been partly out of respect, with the thinking being “Only Ron can wrap up whatever it is he was driving that, so we’ll just proceed from the escape hatch we were given instead of trying to divine intentions he himself might not have mapped out.” Which, by Ron’s own admission, he in fact hadn’t.
Maybe I’m giving too much credit for forward-thinking here, but just look at the way, by intention or by accident, things worked out in the end: Ron was able to complete the statement he was making without having to pretend the other games didn’t exist. Those interim sequels successfully kept the bench warm for the creator’s eventual return -- they didn’t override Ron’s vision so much as postpone it, and it’s probably ungenerous to think this happened entirely by dumb luck. Every team brought their own tastes to the way they grappled with that shoddy seventeenth century electrical wiring, but it was grappled with.
CMI seems to have the reputation of being the Monkey Island game that steers the clearest of the meta-angle that Ron was toiling in, but I think it’s a little underappreciated in this regard. It definitely carries the torch of the first two games in terms of perpetuating that surrealistic undercurrent, the anachronism/fourth wall jokes, and the near-constant theme park evocations. Both Plunder Island and Blood Island have plenty of Disneyland nods both subtle and overt, and of course the entire final act takes place at a danged theme park. The fact is, a game that truly flouted the weirdness of the series and insisted on being a pureblood, risk-adverse pirate adventure with an inflexibly straight face would not look like CMI.
We know Ron wouldn’t have made CMI, but that game’s team was neither unconscious nor careless about recognizing the substructure going on in his games, in my opinion, and they made an earnest attempt to do that aspect justice. In the wake of Ron finally getting to have his say after thirty years, I actually find myself more impressed than ever with the ways the middle chapters walked that tricky line they were lumbered with.