We live in Colorado, too. I don't know where in the state you are, but where I live if the schools are suggesting a skip, it is probably more than necessary. My eldest did a few different things before skipping 5th (homeschool, charter school, GT pull outs, subject acceleration). In terms of in school differentiation, the grade skip has worked the best.
On the other hand, you may have to do a sales job on your ds b/c most schools will use the Iowa Acceleration Scale when approving a skip and a child be opposed is an immediate "no" on the IAS. Could you try to give him opportunities to make friends with the kids in the next grade up though extracurriculars or subject acceleration?
