Rather than always playing "go fetch", why not merchant voyages that could deliver and supply other outposts?
This would run along side the current merchant contracts (perhaps 1 in every 6 or so contracts) but with a slight twist.
Buy a voyage from any outpost merchant.
The merchant supplies you with her surplus stock that other outposts are in need of. Preferably the furthest outposts from where you've bought the contract.
Take the full cargo load and deliver the correct items to the respective outpost.
Outpost 1:
3 X Banana Crates
3 X Barrels of Grog
1 X Exquisite Spices
1 X Fine Sugar
2 X Rare Tea
Outpost 2:
1 X Exotic Silks
2 X Fine Sugar
5 X Gunpowder Kegs
2 X White Chickens
Outpost 3:
1 X Banana Crate
2 X Barrels of Rum
2 X Crates of Cannon Balls
2 X Exquisite Spices
2 X Fine Sugar
1 X Rare Tea
Each outpost pays you a commission upon delivery calculated by items x distance.
Cancel the voyage and the cargo de-spawns.
In this example I chose to have ten items for each stop but that could be altered.
The rep could have a significant increase over regular "go fetch" contracts as you are now a new level of merchant (distributor) and no longer just that one in a million small time poacher / supplier.
Rare, if you really are listening to us, this could be a great way to introduce more handheld variety into the game. Grog and rum barrels, new food types, almost anything.
Crates of weapons, sails, utility items and clothing could all be introduced by merchant voyages (and actually sold to the respective vendor if you prefer).
There could even be unmarked crates of goods with simply coloured labels for identification.
Rare is free to use my ideas. Just scratch my name in a rock somewhere... but not where there are snakes. lol
I would personally prefer to do this type of voyage than any existing quest.