I've learned to never create a situation where friends or family need to press one another for owed money. I've always just paid for reasonable things if frien

I've learned to never create a situation where friends or family need to press one another for owed money. I've always just paid for reasonable things if friends were short on cash. Not because I'm a pillar of charity, but asking for repayment is an unpleasant task. And I'd strongly recommend against renting an apartment or house from family. At best, it adds unwanted dimensions to relationships. At worst, it turns times in life when you would've merely tripped into times when you trip and fall into a snarled briar of family problems.