We lent my parents money and are now trying to tactfully set up a repayment plan. Any suggestions?
Be as straightforward and honest as you can. Explain that you could really use the cash, and suggest a repayment plan that they can comfortably handle. Another option: Mutually agree to set up online payments so that you don't have to constantly discuss the loan, and exchange checks on a regular basis. It works just like any other online bill payment—your parents can log in and just click to transfer funds without you having to say a thing. A site like VirginMoneyUS.com is great for this; so if the loan is big enough, try it (for a small fee).