MIT Mystery Hunt 2020/Moat-er Boats

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Moat-er Boats is a word and lateral-thinking puzzle from the Grand Castle round of the 2020 MIT Mystery Hunt. It revolves around creating chains of types of people (crew members) by linking them together using shared characteristics (boats), ultimately building circular "moats" around central towers.

Solve Path

The first thing a solver should notice is that certain crew members can fit two (or more) different boat descriptions. For example, an ACTRESS "is often miked on stage" based on the pre-placed pieces in the first moat, but they may also be "obsessed with lines", and "their sentences may induce crying".

A green and purple kiosk building, with a single green and purple boat situated next to it in water.
The puzzle's icon, a kiosk presumably renting boats for the castle's moat.

Puzzle Elements