OP, here!
First, thank you everyone for your input and support! I really appreciate it. Being able to vent and get this kind of feedback helps a lot.
This morning went a lot smoother. My son didn't give me any attitude when I checked his backpack and reviewed his work. He was having a mellow morning, which is very nice.
As far as his school goes, while he *technically* has a homeroom, it's just a place for his grade to gather in the morning for announcements. He doesn't have a desk. All EIGHT of his subjects are stuffed into a single binder, which he drags around in a backpack. He has a locker, but he doesn't have regular access to it throughout the day.
Assignments are dropped in a inbox on the teacher's desk, so it's very easy to forget to hand them in.
And the "report card" is beyond useless.

There are no percentages, no grades. It's a masterpiece of computer generated vagueness. He should get a real report card at some point in the spring, but we need to get him on track before then.
You just really nailed it!!!!!
In fact, you just nailed TWO things.
1. First, schoolwork is just NON-negotiable.
You can't reason and 'negotiate' with a kid with a deficit or flaw in their thought process!!!!!
Been there done that MANY times with my son.
I've always been curious about this statement. I mean, I really don't negotiate over homework. If I tell him to do something, he does it. But before I started sending in a homework log book with him, how was I supposed to know if he actually had any homework? The kid's sure wasn't going to tell me! "Do you have any homework?" "No."
I have a daughter who is very mellow. With her, I can say, "This is the way it is," and like magic - it just IS. My son's not like that. He's not defiant, and he's not even a liar (he genuinely thinks he has no homework!), but he questions constantly. And I need to choose carefully when I'm going to lay down the law.
2. See the bolded above.. "because he NEEDS to hear it".
Especially with my son, his LD is known to include the factor that he deals with things auditorily, and has visual processing deficits. He is just not gonna get many things until they are verbalized, very simply and directly, several times.
I think my son's LD is slightly different. When he was little I noticed that I would tell him how to do a math problem and he'd look at me blankly and say, "What?" Then I'd show him on paper how to do it, and he'd get it right away. He was found to have "borderline" hearing as a kindergartner, but because he was ahead academically and quite articulate, the doctors opted not to pursue any medical treatment for him.
With written instructions he tends to only see the end of the instruction. Many times I have to point to something buried in the middle of the paragraph, and he'll say, "Oh, I didn't see that." Even if it's numbered and bulleted, he'll still miss the middle. He doesn't think sequentially (it took me forever to teach him long division!).
I suspect part of my frustration with having to nag him is that I don't even know if he's hearing me, or if he's just hearing Charlie Brown's teacher.
Can't tell you how many times I have responded to my son's occasional negative 'attitude' about schoolwork with... " It is NOT going away... You HAVE to do this... so put a smile on your face and just do it..."
Yes...that simple. (LOVE the Nike slogan!!!!

)

Our phrase is, "Suck it up, buttercup!"
I, too, went through this in middle school and while I'm allegedly gifted, I'm not quite LD (depends on which one of the professionals my parents had me see). Both of my parents were teachers, so some of it was overkill. I have worked in the school system, too. So all of this comes from the heart.
My dad decided I needed to have my homework initialed and then my guidance counselor had to sign off that I had done it. None of this did a bit of good for me.
If a lot of his problem with completing work is the way the assignments are worded, his teachers need to word them differently.
Is his homeroom teacher told to remind him about taking his assignments with him? Are his teachers prompting him directly in class to turn things in? If he's got an IEP, he should be allowed to go back to the homeroom - at least for a little while. It sounds like the whole procedure is overwhelming for him and maybe he would do better adjusting to it a little bit at a time.
It sounds like he's very hard on himself, which is hard to get past until you're succeeding.
I think you need to try to put some of this "nagging" off on his teachers. If its all (or mostly) from you, he won't get it and he'll resent you. If his teachers bug him, too, he'll see that its not just mom going on and on again.

Also, your example about the rough draft - you need to tell the teacher this and have her discuss it with him also.
I don't know how it is in your district, but 8th grade in ours is pretty much a baby version of high school. Its a big change and I had a lot of difficulty my 8th grade year, too.
I would also entertain the idea of seeing a new psych - just a visit or two to get a second opinion. I changed a lot as a person between 7th and 8th grade and I changed my psych at the end of 8th grade and I honestly think 8th grade would have gone better for me if I had changed psychs sooner.

My son IS very hard on himself. It's been an issue since he was a toddler. I almost couldn't discipline him at all, because he'd fall apart if I was even mildly critical. It wasn't an issue because I rarely needed to criticize him, anyway. He was always tried incredibly hard to be perfect. He used to beat his head on the floor when he made mistakes.
I suspect part of what's happened is that he tried too hard for too long and now he's just decided to stop trying. He hasn't experienced what he would consider "success" in a fairly long time, I think.
I don't think we need to find a new psych yet - we've only just started this year with this one, and my son seems to like him.
I'm really hoping high school will be better! It's a different system, with only four classes for the first half of the year, and then four more classes in the second half. It should be easier to track.
Thank you for sharing your experience. I'm hoping I can find a balance between doing just enough, and not too much.
As a teacher of LD/ADHD/ and other special education students...please continue to help your child!
If you can help them learn to be organized it will help them in high school. Also, remember that in high school, they may still need help.
Keep in mind that it is ok to check your child's work. It is also ok to communicate with your child's teacher. Once your child sees success, he will realize how your method is working!
The school should also cooperate and remind your child to turn in the work, etc. Especially if you son is on an IEP...remember they are on an IEP for a reason... and the teachers should support helping him to improve his weak areas. Even you should remember, it is hard to break/change a habit.
I try to use this example when I talk to the general education teachers. I know I NEED to exercise...but I don't! I hear and read TONS of research telling me I should exercise....I still don't. I am out of breath when I walk...I still don't excercise. I don't fit in my clothes real well...I still don't exercise. SO if you get my point, even as adults, we have a difficult time changing our behavior.
Make sure you take time to have fun with your son! You sound like a great mom!
Thank you! I do worry about doing too much for him, but if I look at it as building new habits... well, I can definitely see it'll take time and consistency on my part.
I've noticed some little things - like me putting today's homework log page on top - make a huge difference. Somehow, just having to turn the page himself, seems to make it less likely that he'll carry through with the assignment. So I bought him a new binder today, with extra dividers and a sewn-in pencil case, on the theory that he can't possibly be TOO organized right now.