I'm looking for:
1. Advice for securing accommodations for 2e child above grade level in achievement?
2. Advice for how to use technology to help compensate for his deficit in writing.
I'd second the suggestion to search the threads here for "dysgraphia" - both for advice on accommodations and assistive technology.
Success for both will depend on successful advocacy, and from what you've written, I think the key thing you need first is a better understanding of what the real issue is - vision, fine motor, both. It's hard to know from what you've written if you need more info on reading skills too but that's something else to consider - do you know for sure what the challenge was that the OG targeted, and have you attempted to determine if that specific challenge has been helped through the tutoring.
Once you know for sure what the challenges are - clearly - then you need to think through what your goals are - are you seeking extra educational (instructional, remediation) help or are you seeking accommodations only? That will help you determine whether or not you request an IEP eligibility review or a 504 planning meeting.
Next gather all your data, evidence, work samples etc. Also research your district policy and read up on wrightslaw etc - anything you can find to make sure you understand your rights as a parent and your ds' rights as a student. Collect any articles or research or advice from professionals that is relevant to your child's rights and to your child's diagnoses and needs - to prepare to meet with the school team.
Then you make your written request to the school (for either an IEP eligibility meeting or a 504 planning meeting).
Re assistive technology - we approached this in three directions. I definitely did a lot of research and reading online and it was very helpful. I also located a non-profit organization in our city that specifically helps people with disabilities learn about and try AT, which was also very helpful. Lastly, we advocated for and received an AT eval through the school, but in our situation that was a very difficult and prolonged process (just to get the approval for the eval) and it became evident quickly that the we were getting more thorough and up-to-date info from the non-profit and online research. That didn't mean the school eval wasn't worth doing - it was a necessary step if we'd hoped to have any of ds' AT funded through the school, and we did receive useful input, just not as much as we received elsewhere. So - moral of the AT story (and maybe all advocacy stories) is to spread your net wide and try to research as many sources as possible.
I apologize because that wasn't very *specific* advice - but each child is different and each situation is different. What works for my now-high-school student who relies on an iPad for all writing tasks might not work for your ds in early elementary who may or may not have the same challenges. Even if they have identical challenges and needs, the solutions we used for my ds at your ds' age are probably very different than the solutions you'll choose simply because the term "tablet" had nothing to do with computer technology when my ds was first diagnosed with dysgraphia
Definitely ask here though, and dig through the past threads here - just spending time reading other people's stories helped me a *ton* in figuring out what to do re AT and my ds.
And... having a strong neuropsych report helped too. Our neuropsych gave us a very straightforward "this is what you need to do to support your ds" plan when he was diagnosed - we were told to remediate handwriting to the extent it was possible (and then leave it behind), scribe for him at school starting immediately, get him through one round of OT to get whatever benefits we could (it did improve his posture, gave him an ok pencil grip and improved legibility), teach him to keyboard, and that ultimately he would most likely rely on voice recognition. We didn't get into the nitty gritty details of software or devices (although the neuropsych did have advice on all of that) but the important thing was it was a PLAN forward that helped us know what his future would look like. It was also a series of steps, so we didn't feel like we had to solve it all at once - we started with step A moved on to step B etc, adjusting and flexing along the way. So try to keep it in perspective - read what you can about AT, but start with the diagnosis and understanding what really needs to be addressed.
Sorry for my very long-winded reply - hopefully it's helpful!
polarbear