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.