caluvox said it well. I never loan out more money now than I can afford to "lose". Especially with family members. Through trial and error I have found not to do business with a family member OR loan them money. Sad but true. If I do give it, I do not expect it back. If it comes back, so be it. If not, I knew going in I was giving it away basically.
I will loan any amount to family and very close friends thousands if they need it. Other than that I don't loan money out to people I'm not close to unless it's like $20 then I pretty much just write it off.
I never loan people money. No, wait, I take that back. My mom has borrowed about a hundred bucks from my bank account. My parents borrow money from me all the time. But they always pay it back. But I think my dad still owes me 50 bucks from like, 3 years ago. XD
I loan to family but that is getting old in the tooth. They make it seem like it is you who is being done the service, the favor, when (if) they pay you back. Like i should say Thank you for pay back. family can be the worst to loan to.