Yes. He should get an agents help. Otherwise it all depends on the immigration officer. Ito change my Visa from a-o to O I had to leave the country and come back in on a 60 day. I was questioned. If you have several 60 day passes they see you are not a genuine tourist and can bounce you as, it appears they did today. Regardless of cost, get an agent
Every agent will see it differently. If you are using 60+30 day entries, they may stop you when they see you are not a tourist. I was on a visa and when it expired I came in on the 60 day entry but warned not to do it again. And that was at Suv airport.
Just be aware. Much as you may use the 60 day entry as often as you like in theory, it is possible Immigration will stop you after a number of trips. My 60 day entry was on the page opposite my expired 12 month visa. They could see I wasn't a "tourist" and warned not to do it too often or face denial. Just something to be aware of.