http://www.cracked.com/article_20448_5- ... alize.html
I was thinking of just #5 in that article, the others don't matter or are already there.
How would this work, players that prefer pirating, could give gold to the guild, and when they lose a ship or take damage, the guild gives them back some of it. Not full, maybe 60-80% of what they originally invested, but you get my point.
Saving money for the bad days.
A similar insurance system for traders would be nice too. Not cargo, since it's too cheap to matter, but ships would be nice. It would allow for higher level trader ships for a lower risk.