My son had school based and private OT from age 2 to 8. He had difficulty with most small motor tasks - zippers, buttons, tying shoes, using utensils and, far and near point copying and handwriting. By 3rd grade we decided his skills were adequate to get by in his private school setting - with accommodations such as extra time, models of the alphabet/numbers, graph paper for math, and scribe as needed.
Although we began keyboarding in exerts in 4th grade (and this was not easy, either), he continued to write on his own until 6th. In 6th his school provides laptops for all students and virtually all of his assignments are completed on the computer. Math is still handwritten - and his handwriting is still an issue. It's hard for him to line up his numbers, his legibility is poor etc.
If possible, I think it is important to become proficient with handwriting - the laptop is a great alternative, but it has its limitations. I'd assess how much effort it takes to become proficient and come up with a "goal" that you can live with. Once met, the laptop can remove many barriers and can help the student demonstrate his skills and knowledge without the constraints of poor handwriting.
One thing to consider - my son's Processing Speed Index dropped significantly once he moved from handwriting to the laptop. The neuropsychologist felt that this was primarily due to his grapho=motor skills that had become rusty since he spends much less time writing.
It's all a balance - time spent developing skills is time taken away from others. Accommodations reduce time on task that would otherwise be time to develop weak skills. I try to prioritize and set goals taking into account my son's complex set of needs - there is so much grey area and judgement involved. I don't think there is one right answer.
