What's the best way to spend this money?

First I would concentrate on the loan with the highest interest. I would make the regular monthly payments for the state and federal loans. And I would send $625 to the private school loan. This way that school loan will be paid off in a year. Then I would concentrate on the state loans I would say $1298 to the state loan and it would be paid off in around 5 years. Then you could have the last loan paid off in around 2.7 years without having to pay out of pocket. It will take a while but at least it wont be your money paying for it.