Will agree that it's usually better to give than to lend unless the borrower has a long-time record of financial responsibility.
One exception - my father loaned my wife and I the $10K I needed to go back to school for my second degree. We very carefully drew up a formal loan agreement including terms of repayment (interest-only until I got my second tuition reimbursement check from my employer), and specifically listed it in a declaration of his assets. - in short, everyone was aware of the arrangement We even reported the interest income on his taxes.
I treated this just as I would any other debt and was never late on a interest payment. After the second quarter, I essentially signed over my tuition reimbursement checks to Dad as the principle repayment, and was all set to to pay him back at $400 per month for the balance not covered by TR. My "re-graduation" present was a letter from Dad's attorney stating that the balance of debt was canceled.
Dad made market-rate interest on his savings, the money stayed in the family, and I got a degree that essentially doubled my income within three years. It worked out well - this time!