My 10-year-old daughter just started on the OmniPod on Monday. She did her saline trial on her thigh and her tummy. She put her first Pod with insulin on the back of her arm and has now changed the site to her thigh. She feels like they have all been comfortable spots -- depends more on clothing preferences than anything else I think. Others have suggested the hip/back too -- where you can pinch the "fat" there.
She is in LOVE with it! Her PDM just stays in her "diabetes bag" just like her test kit did before -- and glucose tabs, and ketostix, and glucagon, etc. I think it's really the same concept. Doubt he'll have trouble with it. And... I dropped it the other day on the floor and it was perfectly fine. You can also order rubberized "skins" if you call Insulet -- information at www.myomnipod.com
Good luck!! Let me know how it goes and if you have any other questions.
Oh -- one more thing -- she is drawing on hers with permanent marker before she puts them on. I plan to take photos of all of her drawings and make a collage someday. Kind of a fun thing to do since there isn't much fun about diabetes otherwise... :)