Can you really not put yourself in the mind-set to understand the phrase/advice we are talking about?
What a load of rubbish or you've missed a bit out.
So if my kids asked to borrow money and I didn't see them again it was money well spent? I think not.
You missed out "if you lend money to someone, never get the money back and never see that person ever again, it was money well spent"
It also doesn't take into account how much money, £100 would upset me enough to track them down.
Wow you'd throw money away, what about if it was £1000s?