A couple rules I try to follow regarding money:
Give freely. Lend no more than what you’d pay to measure the integrity of the person in your debt. If the debt is never repaid, you've spent your money wisely.
A good man is charitable without care for recognition. A better man aims to make charity fashionable, even at the loss of the respect of other good men.
please excuse the use of 'men,' it just sounds better than 'people' :-))