Haven't actually set up a teespring fundraising campaign yet, I just took a screenshot and posted that as an idea. Send any PMs with design suggestions over and I can get it up and running if we want to go that route.
He could do a Teespring campaign. Not sure how much he needs to raise but I just threw together a sample with a stock sailboat picture. Maybe someone artsy could vector his head to stick on the front of the tee. With the below setup (front + back) and a price of $20 he would net an estimated $557 once 50 people agreed to purchase a shirt. The $557 is below the $600 figure that would require him to receive a 1099 tax document.