Setting Course for Redemption

The basic structure for events on the ship is based on convincing the captain to set a course for a port you know, determining how long it will take, discovering what happens along the way, and finally arriving. Convincing the captain to change course obviously will require some kind of reaction roll, but what kind? I'm still debating. The captain is, in a sense, mindless. The conversation with the captain will seem almost one-sided, certainly. All I'm sure of is that the PCs can't pick a course for a port until they have established that port in a flashback scene, which is something else I'm working out the details for.

The distance to the port, though, is probably going to be abstract. I thought at first about just rolling for the voyage's duration in days and letting the players pick events that happen during the voyage: the events do "damage" to the "hit points" (days of travel), with more dangerous events doing more damage. Now, however, I'm leaning more towards setting an abstract number for the duration of the voyage, rolling for random events, and ending each event with a roll to see if the duration number is reduced by one.

EXAMPLE: through negotiation with the captain, the voyage duration is set to 5 (perhaps he says "it will be about 5 days".) The GM rolls for a random event; the players deal with that event, then roll 2d6 and pick the highest. If that number is higher than the duration number, the duration is reduced by one: there are only four days left. However, if the players roll doubles on the 2d6 roll, something unfortunate happens as a side effect; what happens depends on the kind of event.