I could write this post myself, about my soon to be 9 year old daughter. Breaks my heart as well but I completely empathize/sympathize with you as far as feeling annoyed some days. Rather, a LOT of days.
One thing, what medication is he on?? My daughter is on Concerta, and in the way of side effects we seem to be doing OK. None that I've noticed, except if I give her her medicine on a non-school day, then she tends to get mopey.. But her teachers don't report that effect in school when she is active, involved and has something to keep her mind on.
Something our Pediatrician told us this year, is that you need to re-assess every year. If it's been 2 years since you've 'titered' his medication, it may not be affective anymore as the meds go based off of weight, and in 2 yrs a kid grows significantly. We didn't realize that and our daughter went 2 years without a titer and we discovered it was time to move her up to the next dosage.
I'm still learning this myself, but one thing we HAVE to realize as parents' of ADHD kids, is that they simply may not be capable for 'taking responsibility' as far as turning in school work, etc. Their brains at this point just aren't wired for it. I am far from perfect at realizing this, but I will work with my daughter to help her realize that there are certain things she needs to be able to do. But in the meantime, it's just as much my job to make sure she is being responsible as it is for her to be responsible, if that makes sense? Kids with ADHD like that need constant reminders. Even when I told the Pediatrician how frustrated we were because we were having to tell her EVERY.SINGLE.DAY what she needs to do in the shower (get wet, wash hair WITH Shampoo, use conditioner, use SOAP to scrub down) and if we didn't or if we just said 'Take a shower' there was no telling WHICH of those steps she would miss, and it would usually be ALL of them with the exception of getting wet. She also needs a timer, otherwise she will be in the shower for 30+ minutes and not have a single thing done, other than being wet. Lol But the Pediatrician told us that this is NORMAL behavior for a kid with ADHD, and that we would just have to constantly remind her.
Another thing that I've been meaning to try (My daughter typically can fall to sleep fairly quickly, although she does have a higher tolerance than her siblings for being able to go to sleep later and get up earlier, which I attribute to the meds), is setting her room up to be as calming as possible. A salt lamp (I've heard these help with behavior after about a week or so), low/calming light, etc.. Maybe get him used to listening to meditation or calming music to wind down at night?
Also, make sure his diet is as free of fake stuff as possible. ANYTHING with Red or Yellow dye can contribute to the hyperactivity. So for us, that means NO cheese crackers, boxed mac 'n' cheese (I make from scratch), a lot of fruit snacks are off limits as well, and a lot of juices. I apply this to ALL my kids (4 total) just so no one is left out. Lol they all have become used to drinking water only (sometimes milk). For Fruit snacks and other snacks, I buy Annies (It's Organic, no artificial colors/ingredients) for those things. It's more expensive, but worth it to me.
I feel for you, it's tough.