Depends on his skills and capabilities. You need to look for locally owned businesses and start knocking on doors till you find, and if he has a desire to work he will find someone. Local business owners are more in a position to have someone working for cash and you can be upfront about it. Almost impossible to get a cash job at McD, or Wal Mart.
In his position, with the insurance, he should work a deal with whoever hires him that some of it will be on the table, even if it 2-3 hours a week, just in case. Just figure the least amount without too much of a penalty from the insurance and get that amount from payroll.
He can also place printed ads in business entrances who have bulletin boards if he can do work "around the house" for neighboors.