Lots of things didn't make sense
I love the game concept, but there were a lot of misses.
First off, ship stats were not readable on the larger ships. The boarding didn't work very well, being difficult to initiate and in one case starting as soon as the battle did. Also, the AI left something to be desired.
My big issue was that it appeared to be no reward for taking towns, making it an expensive and pointless excersize. On a similar note, I would've liked to see more cash rewarded for taking ships as opposed to destroying them. It seemed that there was no connection between the size or number of ships battled and the prize won.