Was he in the same school last year or a different school? If he was at the same school I might try to work with the teachers he has by bringing last year's teachers into the discussion. OTOH, if he's new to this school, I wouldn't bank on making any effective changes in time to help your ds - I'd be looking for a different school.
How large is his current school? Is there only one teacher/class per subject? Do you feel like the emphasis on handwriting etc is a school philosophy or that he somehow just happened to get stuck with traditional-thinking teachers?
I think there is a bigger concern here than simply not being given accommodations for handwriting now because of the frustration for your ds and because he's not being able to fully show his knowledge due to lack of accommodations - my larger concern is that he's also losing valuable time where he could be learning and developing skills related to using those accommodations and therefore he's losing ground for future school years.
I don't know what your "best" option is - there are so many things to consider. I do think if I were in your shoes one thing I absolutely would be doing now is research and networking to try to find out what the environment would really be like in option #2 school if your ds were ever able to get a spot there. If you find out that they are good at working with accommodations and they incorporate technology in their regular classrooms, and it's a school that you like in general, I'd apply for admission even if it's unlikely he'll get in this year.
I am also in agreement with the poster above who suggested not worrying about high school yet, just focus on what to do this year.
I hope things work out - keep us posted!
polarbear
