There are those competitions you can enter like in 99designs. There are some really nice cash prizes.
The company basically gives a specification, then different designers will upload their designs and a the winner will receive the cash. I think you can do about one per week. So see if that's something that can help you out maybe.
This is another way of getting in cash. If he is struggling, while looking for other things, this can help in part. It's not to base his entire career around, but just to be able to make some while finding something.