Sister Drives Luxury SUV But Borrows Money To Pay Bills

Dear Mongoose,
My sister and her family recently bought a very expensive SUV, over $50,000. She loves to brag about it but constantly overdraws her checking account. Back in the fall, she borrowed $700 from me to catch up on her bills. I drive a $8,000 car, but thankfully it's paid for. When should I start asking her about paying me back?

Dear Facebook-only Rich:
This one’s easy, you should have never loaned them the money!  Lay off the 'that’s too harsh stuff already' and listen to me: the number one root to all problems we as Americans face today is THERE IS NO SENSE OF PERSONAL RESPONSIBILITY.  This starts at the top of our government right into our living rooms.  What your sister is most guilty of is the thought that someone else owes her something.  Be it a bail out when she overspends or that she truly deserves a $50,000 SUV. 
 
Call me a Bible thumper, prude, or whatever you wish, but two different verses come to mind when I hear stories like this.  (paraphrased)The borrower is slave to the lender and owe no man nothing but to love him.  Unless your sister cosigned a loan for you, she put herself in this predicament.  If you continue to bail her out well, you’ll continue having to bail her out.  She will have to ultimately realize that if you have more $ going out than you have coming in (and you’re not the US Government with money printing presses), you will not only run out of money but you will owe someone more than you’ll ever be able to pay back unless you cut expenses or bring more in.  It sounds simple and all ties into personal responsibility. 
 
On the lighter side try this, if you have a soft spot and feel the need to bail her out again, at least get something in trade.  It doesn’t matter if its house cleaning or using her fancy truck, don’t just “loan” her the money without something imminently in exchange.