Here's a perfect example of what's wrong with this game.  I was asked by a governor to go build a school in Corpus Christi.  OK, I went to Corpus Christi and started trading with that town, because before you can build anything in a town, you need a building permit, and before you can buy a building permit, you have to impress the locals by delivering a ton of goods.  I spent most of my allotted time currying favor with Corpus Christi, until finally I had enough merit to buy a building permit--only to be told that my rank was not high enough to have more than three building permits in the Caribbean, and I already had three.  I should come back when my rank is higher.  Of course, time expired and my mission failed.  The governor was "very angry" with me.

OK, what's the point of sending someone on a mission that can't be completed?  That's not fun.  That's just a waste of time.  (And you know what's really unfair about this?  All those offending building permits were awarded to me for free for earlier service.  I didn't even have a choice.)

Another problem: you can set up automatic trade routes to trade at the docks of various towns, and this nets you some easy money, but it won't do what you really need it to do: your automated captain cannot access your own warehouse if you have one in the town.  That means your sugar plantation in one town cannot automatically supply your rum distillery in another town.  You have to keep MANUALLY sailing from one town to the other, loading sugar, unloading sugar, loading rum, unloading rum.  Do you know how boring that gets?  Buy the game if you want to find out.
Here's a perfect example of what's wrong with this game. I was asked by a governor to go build a school in Corpus Christi. OK, I went to Corpus Christi and started trading with that town, because before you can build anything in a town, you need a building permit, and before you can buy a building permit, you have to impress the locals by delivering a ton of goods. I spent most of my allotted time currying favor with Corpus Christi, until finally I had enough merit to buy a building permit--only to be told that my rank was not high enough to have more than three building permits in the Caribbean, and I already had three. I should come back when my rank is higher. Of course, time expired and my mission failed. The governor was "very angry" with me. OK, what's the point of sending someone on a mission that can't be completed? That's not fun. That's just a waste of time. (And you know what's really unfair about this? All those offending building permits were awarded to me for free for earlier service. I didn't even have a choice. )

Another problem: you can set up automatic trade routes to trade at the docks of various towns, and this nets you some easy money, but it won't do what you really need it to do: your automated captain cannot access your own warehouse if you have one in the town. That means your sugar plantation in one town cannot automatically supply your rum distillery in another town. You have to keep MANUALLY sailing from one town to the other, loading sugar, unloading sugar, loading rum, unloading rum. Do you know how boring that gets? Buy the game if you want to find out.