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Prepayed Rent Situation

Last year, I needed extra cash in January for an investment project and my roommate paid 11 months rent in advance and I gave him December for free.

This year, I have no need for cash (other than to stockpile for when I finally start buying stuff), but he wants to prepay again. By doing so, he wipes out his savings account, so that when he files for financial aid, he doesn't have much money saved up, so he'll get more aid money.

Since I have no pressing use for cash (except for paying down my 6% mortgage, which is worth only 4.5% after tax), I'm not sure I want to do this again. I could see doing it for a half-month free, which would be around 4% discount for him.

He's a good roommate, quiet, studies a lot, and my dog likes him. He's finishing up his 2nd year at a community college and will be transfering to nearby 4 year school to finish his bachelor's degree.

Any thoughts? Have other people done transactions like this?


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