Nice! Amazing you got to ask him. However... the image you show is the EGA version. Iain McCaig drew the VGA portraits, not the EGA ones.
See the Mojo article
https://mixnmojo.com/features/sitefeatures/Revealed-Iain-McCaig-the-man-behind-the-Monkey-Island-VGA-portraits
I'll get to the bottom of "Loom Sucks", I just haven't talked to the right people yet.
Regarding Elaine being Avril Harrison, I mentioned it in my conversation with Prince of Persia creator, Jordan Mechner.
Amazing we're getting all these incredible stories. Thanks for your work Daniel!
There's always more questions. I wonder if you'll ever get more details. (like who wrote "LOOM SUCKS" and it would be amazing to see photos of the original LucasArts alumni that Iain McCaig clearly (albeit loosely) based his MI1 VGA portraits on (Guybrush is clearly a self-portrait, for example and Elaine was Avril Harrison, etc. etc)).
👕 I beat #MojoleXtremiest #871 and all I got was this stupid t-shirt. 4/6
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https://funzone.mixnmojo.com/Mojole/