Get a job and it should be easy to do.
Now if you said $10,000 in one week that might be a different story, but $10,000 in 2 month is nothing
bet on sports.. duh
He's in Iowa City they don't have any ponies/casino's any form of gambling so this should help him save money!
Don't go from one vice to another, work your ass off for a year with a job at your local quik-mart and put all the money in the till and pay your living expenses with this income.
Then get a second full-time job anywhere thats hiring. Put this pay in the bank and after 6 months off working your buns off I imagine you'll have a new outlook...
BTW you may qualify for some relief by the Goverment on your student loan? Good Luck