It is good to be generous, but peoples like this that I have known must be sure to understand that it is your generosity and not fear that compels you. If you show anything that can be interpreted as fear or you let down on a rule just the slightest, you will have trouble.
There is something familiar about this man. I may have met him in my travels. If it is the same man, his wisdom and advice are solid. I worry about your settlement, though. Could it be that you have a leak somewhere?