Has your district ruled out dysgraphia? It seems remedial instruction from an OT to address your concerns would make sense and not be terribly time consuming or use too much in the way of resources. I just ran the question by DD and she feels strongly they have to determine if he's actually dysgraphic. "If he's dysgraphic it's not going to make any difference for him." Just a bit of btdt advice from one 2e kid to another...
Can I say how much I love this? Please let her know for me that I really value her input. The school psych is in two minds about the dysgraphia dx. He has some of the hallmarks of dysgraphia but not all. Then again, she recognizes that he compensates mightily. But your DD is absolutely thinking in the way I am: we need to know if he can learn to hand write before sinking a lot of time and effort (and inevitable tears) into all this.
I did a lot of calling around and calling in favors in the last few days, and I found an OT that seems like she's keen to meet a 2e kid and will devise a way to evaluate the hypotheses at hand: (1) his handwriting is a result of missed educational opportunity due to skipping 1st grade or (2) he has dysgraphia.
But wow, the "middle schoolers can't learn handwriting" concept is rampant. I had a few snippy phone calls with OTs where clearly I was unaccepting of reality. Hopefully the OT I found can give us a path forward.
DS is also devising his own version of Handwriting Without Tears with remarkably clear goals -- heavy on the motivational peppermint patties and drawing strongly on his experience as a violinist. He wants his handwriting to be legible at a moderate writing pace - fast enough he can keep a sentence in his head. I'm going to do it his way to start because he has a plan. For all this, he's been the one most able to predict what will and won't work, so who knows, maybe we'll get somewhere.
Now off to buy a huge bag of Yorks...