He's never been great about doing his homework, multiple excuses: didn't know, didn't get any, and nothing to work ahead on.
Aside from the excuses, when he *does* do his homework, have you noticed anything that's stressful for him or seems more difficult than you'd expect? Does he seem disorganized in general or only with respect to homework?
If you see issues with either of these, it's possible there's more going on than simply lack of motivation.
[i][b]Well, yes. Last year he was in Advanced Literacy, and this year he has been moved up to Advanced Math. Math doesn't come easy for him, but he had an amazing teacher last year who brought out the very best in him. Math takes him a LONG time. Sometimes several hours. He can only continue along on this track of advanced classes if he gets a B in the class, so he is motivated by that, and sinks all of his time into that. Frankly, I think he's fried after that. [/b][/i]Last year, I was on him to get his work done, and frankly, it was obvious that I was putting more work into this...the worry at least, and our relationship became quite strained. "Leave me alone you helicopter parent!!"
Were you watching over him, or were you helping him find strategies to stay on track? How you approach the situation can make a big difference in terms of whether or not a parent's help is accepted. It's easy to get stressed out as a parent when you think about the consequences of not turning in homework etc, but instead of focusing on that, try looking at it as a project to solve together. *IF* you truly think the challenge is a lack of organizational skills, ask your ds what the actual challenges are - what makes it tough to turn in his homework or to remember to do it, etc. Ask how homework is handled in each class. You can research and come up with ideas and strategies he can use, but instead of telling him to do them, ask for his ideas first, suggest things you think might help also, and come up with a plan together. Then act as a partner in helping him stay on track with the plan. Let him take ownership of it, but check in and adjust as needed - basically act as a mentor. In the event you think this just won't work for your ds (for whatever reason) - because you're his parent, find someone who you can ask to mentor him in organizational skills, keeping up with homework etc. It could be an adult organizational coach/tutor or a high school student that you're instructing.. whatever might work in your situation.
He honestly just wants me to stay out of it totally. That way, if he's burned out, and I insist that he finish something rather than going to bed, he can get out of it, without the pressure. 
OTOH, if you think it's an issue with motivation, that's a different type of challenge. The first thing I'd recommend - don't panic. He's only 14, and only in 8th grade. He might simply not have found his inner motivation yet. Maybe the subjects he's taking in school simply aren't that exciting to him, maybe his teachers aren't inspirational, maybe he'd just rather be with friends right now. Maybe something else entirely is going on and it's interfering with school. The key here is communication, keeping the lines of communication open, trying to know your ds as much as possible.
I agreed with this, and am trying not to panic, but I worry that we're now into the last 1/2 of 8th grade, and HS is just around the corner. Yikes! I reminded him that if he completed his work routinely, I'd be able to back off. He was doing the school work, but only by being prompted and reminded by me. We've tried consequences, but nothing was too effective.
A few random opinions from me on this: re backing off, if you're sure he's not facing a true organizational challenge and lack of motivation is the issue, it's ok to back off and let him sink at this point. He's still very young and he's not in high school yet. These grades, this year, aren't going on a college application. If he needs to sink a bit to find his motivation, now's the time to sink. Totally jmo, and I'm not a professional so really truly take what I say as my opinion only.
There have been some girls interested in him which has been a real problem. He's really not socially mature enough to handle these "relationships", and they've created much drama and emotion for him...that he doesn't handle well.
I've been through middle school with three kids - one ds and two dds. My experience with girls going through puberty and middle school (both my dds and my ds' classmates who were girls) is that the emotions are *nuts*, all over the place. I don't know what the answer for your ds is, but if there's a way you can find to help him get interested in something outside of girls or into a different social setting it might help quite a bit.
YES!!! He has big college dreams, but seems totally unrealistic considering his lack of effort.
Again, this is jmo, but none of my kids have had very realistic long-term insight into what they wanted out of life at 14. (Possibly my children aren't all that "high ability" when it comes to long-term planning lol! My oldest really found his motivation mid-way through high school. Would it have been nice for him to understand how effort put in during middle school might pay off later on? Sure! But at the same time, nothing from middle school (here) carries through in a way that diminishes anything he's done since he found his direction. Grades from middle school (here) end as of middle school. Yes, they exist in students' files possibly forever, but they don't get reported anywhere past applying for high school programs, and few of our local high school programs even look at grades. My ds had a semi-impressive honor award during middle school, but it's not really relevant at this point and it's something he can't use for college apps because it's too far back in time. Middle school fades quickly into memory once you get to high school.
In terms of organization, he's not an organized kid, but to compound things, they don't have lockers and have to exist out of a backpack for the day...often stuffing work into his backpack just to get to the next class on time.
This made me giggle just a little bit - my ds is 2e and has dealt with a lot of organizational challenges. In high school he's used his backpack as his locker - he likes having everything with him in one place, and he worries that if he took the time to go to his locker he would be late for his next class, as well as quite possibly accidentally leave the wrong books/papers in his locker. I thought that was just my organizationally challenged ds... until my dd went to high school and she also leaves everything in her backpack and carries it around all day - and all of her classes are within just a few feet of each other and her locker. She does it for the very same reason ds does - it's easier from her perspective. They both stay fairly well organized this way - dd has no trouble with it, ds has a bit more of a challenge putting papers actually into his notebooks, but those were things we've worked through together for a few years and he's getting the hang of it.
He loves video games/xbox, etc. It's one motivator that works, but I'm worried that if I say, you can have 30 minutes of xbox when your work is done, that he either rushes thru his work, or has "none", and just reads instead. We do require an hour min of work.
Is it possible shorter work times and short breaks between might work better? Can you work in any breaks where he's up and active rather than passively playing video games? Are you just afraid that he'll take advantage of the games as a reward or has that actually happened? If you haven't had it happen yet, and video game time is a motivator, I'd try it out. If it doesn't work, move on to something else.
He doesn't transition well from task to task. So, he usually needs to stay focused on one thing till he's done, and then move on 
Thanks for all of your great advice and support!!Best wishes,
polarbear
