I was enjoying the game until I got to the kraken, then I gave up on it. The kraken fight was poorly done. You can get to it long before you can kill it, at which point there's nothing left to do but grind until your ship is good enough. No amount of skill will allow you to beat the kraken without grinding for upgrades.
After you upgrade your hotel, borrow the max amount and build as many of the new rooms as you can afford. Your customers start to get upset if you do not immediately have the rooms ready, and your reputation will suffer. You will end up with negative money and a ton of debt for a while, but your rep/income should not suffer while you are paying it off.
It's funny how I can send a guy to scout out a farm and he sees turnips all over the place. Then when I go to scavenge, all we can find is an apple tree.