San Diego is a expense place to live but there are areas in and around San Diego where the rent and cost of living is not as expensive. East of Oceanside (where Camp Pendleton the USMC base is near) are smaller towns cheaper with more affordable housing but are close enough for a Uber driver to have a great business. In addition to fares to and from the airport, there is the train station where day commuters arrive needing transportation to various areas of the city. Tourism is big in San Diego, with many attraction in or close by. The Marine Corps base  could provide him with business as well.
He is a very smart man, a survivor and a winner as a father so I am sure he will land on his feet where ever he goes ! 
The biggest disservice that the "system" and "certain society" makes is to take away a person's self-respect and self-worth
The old adage, give a man a fish and you feed him, teach a man to fish and he feeds his family. He feeds his family with his own hands and not a hand-out.