Personally I don't think the let him go on his own and see where he is in 6th grade approach is a great idea. DD has been explicitly taught everything and it has been a long, arduous process to get where she is. Her comprehension is sky high but she totally lacks automaticity. Things that come naturally to other kids just don't happen that way for her. I think this is a processing issue so probably common in dysgraphic kids. We had a debate as to the best way to teach her to type (actually 'keyboard' as typing apparently implies using a formal home row/ 10 fingers approach...) and ended up encouraging her to use a home row system but still allowing her to do what worked best for her. Her visual processing was so bad they had to start with training her to scan the keyboard to find the correct letter. When she started I believe it could take almost a full minute to locate a particular letter key. She never would have become functional left to her own devices. But that's my DD - your kid could be a totally different story.
And one point I left out of the cursive discussion - it is sometimes easier because the pencil doesn't leave the page so spacing is less of an issue. Some dysgraphic kids eventually develop their own style of handwriting that's not quite printing, not quite script. I think that may be where DD is now which is why it has become easier for her to write short notes that are at least somewhat legible.
We started with oral responses, *no* copying and scribing. It was ok in 2nd grade when the work load was lower (and no one at the public really had any idea what to do with such an outside the box kid). However it is much better to allow them to move towards independence. At least with my DD it takes her so much longer to learn to do these things that we need to have a plan in place for several years in order for her to function as needed at higher grade levels. In other words working in 3rd and 4th grade on these skills allowed her to have a great year in 5th. 6th grade will be a year to see where she is and what needs to be added or changed so she will be able to function as well as possible in 7th.
DD's school implements things across the board. In other words her OT time may occur during computer lab or a writing block so the skills aren't developed in a vacuum. Just like its harder for her to learn these skills it's also harder for her to transfer them. Back to that lack of automaticity thing again...
Oh and one of the first things AT wise that DD learned to do independently was PowerPoint. Great entree that made her oh so much more comfortable with it all. She also does/did spelling through an app called Spelling City. She said the app that allowed her to photograph and write on worksheets using the iPad was called snap something - don't remember the exact name.
AT specialist (I believe) can come from an OT or spec Ed background. Check with your local university. Also your school district can direct you even if you are in a private.
I'm glad Polarbear and Spaghetti weighed in - their kids are older and they have many years of practical experience. Hopefully DeeDee will wander by too. Such great resources on this board!
