Well, it can't go down any lower than Horror of the High Seas. Problem then (depending on who you ask *cough* Skull *cough <img src="http://www.piratesahoy.com/forum/style_emoticons/<#EMO_DIR#>/tongue.gif" style="vertical-align:middle" emoid=":blah:" border="0" alt="tongue.gif" /> ) is that of course you cannot go anywhere except QC to do any major business. There are other pirate forts around the archipelago, but QC is the only one with a shipyard ... and brothel. <img src="http://www.piratesahoy.com/forum/style_emoticons/<#EMO_DIR#>/wink.gif" style="vertical-align:middle" emoid="
" border="0" alt="wink.gif" /> ("You told me you loved me!") - lol
I am unsure however, if you knock up your reputation will it continue to go down due to not paying back the loan shark. Common sense would be 'Yes', however not all things are as they seem, so perhaps someone else might be able to answer the question for you. <img src="http://www.piratesahoy.com/forum/style_emoticons/<#EMO_DIR#>/yes.gif" style="vertical-align:middle" emoid="
" border="0" alt="yes.gif" />
All in all, there really isn't a major need to borrow from the loan shark. If you are at the beginning of the game, you can overtake a French or Pirate vessel fairly easy (watch out for those damned trapped chests if you're small on stats ... ugh), and you don't always have to get in a fight. When you engage an enemy, you are far enough away to back out if you feel like it.
Churches don't seem to be a major help in getting your rep up now it seems. I gave the church a couple 100k, and it didn't do a damn thing. However, I tell a couple people about their purses being exposed and I go from a Horror on the High Seas to a Swindler. ...go fig.