I blame http://www.furaffinity.net/view/15355389/ for reigniting my desire for an inflatable Yoshi so looking at that take on him (hence the arm position) and the Amiibo I bought recently I modeled him again. Also using texture painting in Blender really helps with these things.

I'm thinking one chamber for the head, one for the body. Not sure about the valve placement, I'm sure the huggot would put it on the front of the mouth :P. The body is rounder and includes the shell for more softness and having more to hug, probably would have to be made smaller if he was turned into a latex toy to account for ballooning. I'm thinking a strong strip of latex around the base of the nose to keep that indentation there.