@Jimmy *********
m okay what caused the confusion (on your part) is confusing 30 day visa exempt entries by AIR (which have no official limit) and 30 day visa exempt entries by land (which have a limit of TWO entries in a calendar year).
He's only flown in, he's flying in again and as long as there's not some other entry history that we don't know about (like living here on back-2-back 30 day visa exempt or 60 day tourist visa entries) there shouldn't be any problem stamping in..