Have you had his visual/motor skills tested? In 1st grade public school teacher told me my son would be one of those children that used the computer instead of handwriting! By second grade, I suspected trouble. I talked to our pediatrician and had him professionally tested. We discovered spacial and visual dysgraphia and he was prescribed OT for 6 months with a professional. It definitely helped his confidence. Rest assured, bad handwriting skills once learned are hard to break, so the pro did not work on his horrid printing skills; instead she helped him master cursive. Get on top of it, because what I found was that my son was reluctant to write what was in his wonderful mind because it was too much trouble! A gifted kid in every other way. There's lots of books out there on dysgraphia, check your local library.
Hope that helps,
Jeanne
By the way, my sone is almost 10, and also learned from HWT,a great resource.