Can they differentiate and keep him in the same grade? Will they let him type instead of write? Do you think he could socially handle being 9 and in middle school around 11-12 year olds (6th grade)?

Wolf is homeschooled through an independent study program and his penmanship is age level, but he's had one grade skip and is working 2-6 grade levels above his age everywhere but handwriting. If it were him, I'd say skip him, but then he is very socially adept and extremely resilient. Only you know if your son will be able to manage it.