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This is overall pretty amusing, but I'm stumped. I know basically everything I need to do (including a rough idea of how to get through the door with power suit in hand), but I can only find three Gems--one between the buildings, one among Craigo's boulders, and one dropped by the fedora dude. Any hints on where to make up the remaining three?

Attempting to buy the boulders is a trigger that allows you to look for gems in some places (such as the one in Craigo's shop). Try re-inspecting some things that you looked at earlier.

Ah, that did it, thank ya! On to the next.

Congrats!