MIT Mystery Hunt 2020/Moat-er Boats

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".

One can assemble six complete moats of eight pieces each in this manner, using the pre-placed pieces as a guideline. One can now turn to the numbers on the moat pieces and the red-colored letters. Noting that there are exactly two red letters in each job title and at most one number on each side of the job title, one can associate each red letter with a number. For example, the C in the preplaced ACTRESS can be associated with the 3 on the preplaced moat.

Next, one can note that the numbers within any given moat compose a sequence from 1 to N. Assembling the letters in this order spells the name of a naval captain—in the first moat, this is JACK T COLTON, captain of the Angelina.

As it turns out, every naval captain in the puzzle runs a boat with a name eight letters long—exactly the number of pieces in each moat. Each moat piece also has a space underneath the boat for a single letter. The boat pictures in the puzzle sail clockwise, so the name should also be entered clockwise using the pre-placed pieces as guidelines.

One can now turn to the central turret in each moat, and note that the letters spell out the word SIGNAL; in addition, the captain's arms are each marked with a lowercase Roman numeral, and each piece in the moat is associated with a cardinal or ordinal direction. This is a clue that semaphore is important to the puzzle. In fact, by arranging the captain's arms to form the letter on the turret in semaphore, one can associate each Roman numeral with a letter from the ship's name. For example, the letter S points west and southeast; the letters pointed to are A and L, respectively, which associate to the numerals ii and vi. Noting that the Roman numerals also run a sequence from i to xii, one can arrange the letters in this order for the final answer,.

Puzzle Elements
Hint In Flavourtext - The flavourtext mentions both "versatile crewmembers", hinting at the shared characteristics, and emphasizes the presence of both "captains" and "their ships", further cluing the connection between famous captains and their respective boats.

Shared Characteristics - The majority of this puzzle is finding two people that can be described by the same sentence, often with creative interpretation of the words (such as a TODDLER and a LIFEGUARD both being people who "sit in a high chair").

Marked Letters - For each person, one or two letters are colored red. When combined with the numbers that are next to each of them when placed properly, solvers can reorder these marked letters to form...

Famous People - ...famous naval captains (all fictional)! Of course, being captains means solvers can also identify their...

Famous Vehicles - ...boats (except in one case where it's a u-boat)! Notably, each one is the same length (8 letters).

Letter Placement - As solvers assemble the moats, they might notice that each moat piece (with a picture of a bumper boat on it) has a slot underneath the boat for a single letter. Once assembled, this allows for the placement of an eight-letter word—the name of a boat, to be exact.

Semaphore - The "moats" are each composed of eight pieces, each one corresponding to a cardinal or ordinal direction. Unlike puzzles that extract directions and translate them into letters using semaphore, this puzzle requires solvers to use the captains' hands to spell the semaphore for SIGNAL (as written on the towers). Doing so will single out two letters of the famous boats per moat, which can then be reordered based on the roman numerals next to each of the captains' arms to get the final answer.

Asked and Answered - The puzzle asks for "someone else who really loves the water"—this query is answered with the final answer: a noted marine biologist and environmentalist.