Craig, I would def. have him checked out. As you probably know, kids show their discomfort the only way they know how, by crying. Could be the ear, constipation, whatever.
We thought Kayla had colic for most of her First and second year of life. Looking back, I really think now that she may have had reflux. All my friends kids take something for reflux and they were like kayla was. Anyways, I dont know how they test for that, but I know it did wonders for their collicy kids. I wish I could remember the name but its a common adult reflux drug as well.
Good luck, I feel your pain with a collicy child, nothing like seeing your child suffer! Its very heartbreaking and exhausting.
Karen ~ Wife to Troy