Just a couple of simple things:
- whenever your food supply ends, it'd be useful an "autoequip" function that put one of the food items into the correct slot (maybe putting in the one that is cheaper would be a good idea, since when you are in the shop you can always fetch a better price);
- add an option to wait on the map like the other convoys (pressing the space key to pause/unpause), sometimes it can be useful waiting instead of clicking here and there just to wait some time in a fixed point;
- make the time pass even when you're in town, maybe when changing map (Merchant--->Smithy or Zendar's town square--->Arena). I'm not sure of this maybe it already increment the time (I haven't checked, my fault).
Finally, I'm sure this one has already been thought, but since I'm here... Adding the possibility to attack every convoy you come across via conversation.
BTW, keep up the good work! Can't stop thanking you for this masterpiece! Reminds me of Sid Meier's Pirates! a bit, but battles here are way more funny!!! You bested Sid

!!!
P.S.: Maybe I used the word maybe a bit much eh!?