As a fun little experiment I made an “example entry” for the challenge to better illustrate the kind of thing I was looking for (though not really that complicated).
Grim Zeus combo
(40) Zeus + Crimson Angel (RotF LE version), Grim the Savage (FN version), Gentleman Jocard, helmsman
(12) Tiger’s Paw + Calypso, Ms. Cheng
(28) Frontier + Nikos Chelios, Ralph David (RV version), helmsman, oarsman
Here we have a rerolling Tiger’s Paw creating whirlpools with Calypso that the Zeus uses to steal a ton of gold from enemy HI’s. The Frontier tries to steal enemy treasures and +2 each one, using her hoist crane to explore the home island without docking at it due to Ex-Patriot/Mercenary (preferably offloading one at a time for maximum +2’s). The Zeus provides deterrence through pure firepower while the Frontier can also run gold conventionally to keep the fleet effective. The Paw cannot be boarded while she has panels and provides a unique spot for Calypso to call home. In a perfect game Grim would steal a ton of gold that is then taken off slowly by the Frontier for a crazy amount of bonuses. This fleet uses 3 of the challenge-required crew (who likely work synergistically to boot) along with 4 additional named crew. The key players stay face down as long as possible with some surprise element likely. (an opponent is likely to guess that it’s Grim on the Zeus, but Chelios and the non-RotF Ralph David could be a small shock)