What I learned from this is that the district HAS to see the real child if they are going to recognize their needs. You have said repeatedly how much support you provide (perhaps it is scaffolding or perhaps it goes beyond that level - I can't tell for sure) and how you are tempted to let him go to school as he really is. You have expressed that you don't think it would be fair to your DS to do this though. Based on the story above I think it may be time to do this. How can they know what he *really* needs if you are protecting him from showing it? How much time does your school handbook say is age/grade appropriate? What would happen if you didn't assist with homework and set a timer for the amount of time they say he should be spending? Let them know in advance you will be removing the scaffolding and supports for a week and let him just function on his own. One of 2 things is likely to happen - either he will rise to the occasion and you will see capabilities you may not have known were there or the school will be forced to see the level at which he is actually functioning. You can't fix what you don't know is there. This may feel all wrong to you but I think it may be a necessary step in the advocacy process for you.
I was just reviewing this post and something struck me. This is funny (but not ha ha funny): they SAW DS last year, all of his struggles, he circled the drain all year. Of course I had to step in, because he was having a psychiatric crisis. The program's answer to DS is: we don't want him here, really, and if he requires extra work that proves he doesn't belong.
The point I tried to make all year last year is that the nature of his problems goes with him wherever. No teacher is going to relish all the 504 accommodations. No teacher is going to enjoy his personality when he is overwhelmed, anxious, depressed. There has never been a single person who stated a single "academic concern" about his ability. Their take is that this is too much rigor for him. My take is that my friends with kids in "regular" programming have just as much, if not more, homework, rote learning, busy work, etc. And neuropsych said we do not want to let him off the hook, challenge wise. I think part of the problem is he's never had to try before, so he never developed good habits.
If it didn't hurt DS emotionally to throw him to the wolves (i.e. stop the scaffolding), I'd do it. I can't do that in good conscience when I'm most concerned about his mental health.
