Using Canoes and Island #14 could also get ugly real quick. As mentioned, the canoes don’t have masts and so would be unaffected (I think) by the 1-2 result, meaning you’d only need to roll a 5-6 to potentially add up to 5 Events to your fleet. If you’re very lucky you can skip out on Hidden Cove or Favor of the Gods in your initial fleet build and grab those two with the first successes, then grab either Mermaids, Becalmed, Duel or any of the other Events that hinder ships. This would save points in the overall fleet, allowing for either more/another ship or more crew on a particular ship.
1-2: Roll 5d6. For every 4-6 result, eliminate one of this ship’s masts.
3-4: No effect.
5-6: You can add an event from your collection to your fleet.
For island #4 I assume you’d need to choose a Treasure that could actually be loaded, as opposed to one that would go face-up on the island? If not, you could intentionally bring in Wolves to keep that islands gold from being taken, then re-dock and if luck is with you you can select either Pirata Codex or Jailhouse Dog to get rid of the Wolves so you can take that islands gold for yourself.
Odin Missile does seem like a go-to combo, but you could also bring in a treasure that modifies gold values to help win, something like Jade or Spices.