Maybe he is looking to maximize his time in Thailand. It would make sense to enter visa exempt for 60 days, apply for 30 day extension and then change to Non-O once on the 30 day extension.
Check with the Immigration office. I extended one time for 60 days (visit family) on visa exempt entry. They would not give me the initial 30 day extension, after I had asked about the 60 day family extension. Only the one time 60 day visit family extension.