fahbs: I'm finding it insanely profitable to turn pirate. You get 6000-7000 just from auctioning the ship plus all that free cargo. Maybe 1 in 4 you'll get caught and fined but the fines never exceed the profit from one ship. There's the reputation penalty but it's impossible really gauge who damaging that is.
Ghorpm: Try to do the same on the hardest difficulty :D You will get such a huge fine it'll make your head spin! ;) Actually you can get an astronomical fine even if you are a good boy - The Church may accuse you that you believe that the world is round. Of course you'll be found guilty and a loan will be your only option to stay in the business a little bit longer ;)
I've actually escaped from that fate, but I'd already bribed two people in the bath house. I also tried everything I could at the church (donation, extension - even feeding the poor). I probably started some civic projects like roads and wells, too. While I think "believe in a round world" might be solely related to church attendance in the game, it can't hurt to help your town reputation as well.