Haha you guys are hilarious. Oh and don't mind my low post count, but anyways, if a noob attacks a guard it will drop items/cash.
So hey if you want to be stupid and lose some mets then go right ahead. Just have the noob die to a regular dove and voila you'll be on the last set of islands then have it die once more and there you go.
Stone city will be your destination without losing a thing before that. I'll repeat, go ahead and be stupid by losing mets/gems/scrolls by attacking the guard
Oh and yes, I tested this out long time ago right when CO2 Alpha came out and tested it many times on CO 2.0 as well.
Long story short: Attack a guard if you're stupid. Die to a creature if you're smart