2.Not rules question, some thoughts about turn order determination by ship capacity. It is an advantage for leading player - usually who has most capacity is potential leader. So he gets turn to play last, maybe there are less resources left, but other 5 players has already by playing cards reduced blockade levels and increased port defences - so leader has less risk to move ships and gets more advantage to buy/sell goods with his capacity.
There is not much incentive in this game to play cards to reduce blockade when other players can benefit from that without expending an action. And it's probably even rarer for players to keep decreasing the blockade so that the last player gets a benefit that the first player did not have. I.e., the following situation won't happen often: first player lowers blockade in Charleston from 4 to 3 and moves in; later, the second player lowers it from 3 to 2 and moves in; finally, the third player now faces a level 2 blockade (an advantage over the second player) and has not lost any action for this (an advantage over both other players).
The first player in game has biggest risks and lowest capacity, so he is limited in his actions or takes big riks. Maybe someone tried to play game in reverse turn order?
What the first player lacks in capacity he can make up in black market goods or tobacco. Especially with tobacco, there are not that many sources and it is giving you enough of a profit over cotton to make up for a smaller capacity. Last player will most likely not be able to find the best goods in enough quantity to fill their larger capacity, so they'll have to settle for less profitable goods.
And once this approach seems to stop being profitable, you can always bid for a ship and get to be the last player.