With regards to gold at the start, you're right in that it's relatively easy to find, but it's even easier to die when you have no weapons, no armour, low stats etc. If possible, it might be an idea to set it up so that the enemies you face on the main town's map are both easy to kill and also that the gold is a bit easier to find - of course, to counter the ease of getting gold I would suggest making it harder to get anything decent in this map weapon/armour-wise. Same goes for the town, of course. You should have it set so that you build yourself up in the initial map in order to get the hang of things and then venture out into more difficult areas. Does the purple town have exactly the same weapons? I forget.

I'm not sure if that's doable, but it would certainly be ideal.

EDIT: On a sidenote, saving, exiting and restarting fixed The Captain's counting problem, too.