Cathy - Please don't worry about letting him type everything - I think that it's a very reasonable way to approach the asynchrony involved with 4+ level work. If you "really" want to work on handwriting "Handwriting without tears" for example, make it "in addition" to his other work, not as any variety of gatekeeper.
You can try an OT to evaluate handwriting, but I'm not enthusiastic about what level of advice you'll get. Other ideas are: calligraphy, drawing class, handwriting improvement books from the library, handwriting analysis books for a "top-down" approach.
Willa - I'm sorry to hear about your own medical issues - oh well!
Best Wishes,
Trinity
