Cleaning Rooms

One of the fun things with Roger is cleaning his room. The place looks like a bomb hit it on a daily basis. Some of this has to do with he is a kid, I probably don't get on him as much as I should about it, and the executive functioning disorder plays a big part as well.
He has no organization at all, not at home, not with homework, and not at school. He just does not get it. One example is his room. He will walk in and not know where to start so he just doesn't do it. If it gets clean like it should I either have to do it myself or stand there and watch and give directions step by step. We have gotten to the point if I can at least see a good portion of the floor, walk through the room, not see trash, and the clothes are put away fine. (we also have 3 boys in one room so that's a lot of stuff.) On the other side Lucy is insane about where things go in her room, she can tell if you move something.
Another is homework. He will do his homework (if he doesn't leave it at school) put it in his backpack but by the time he gets to school he doesn't know where it is. Usually it is found on the bottom of his backpack all crumpled up. Folders do not help. In the past the only thing that helps is for him to type his homework or at least what he can and email it to the teacher, this works for stuff like spelling sentences and stuff but usually doesn't work for worksheets.
All of his teachers throughout the years have said he has no organization at all. He can't find pencils, paper you name it. In 1st grade a bag of blueberries got pushed to the front of his desk, they were found at the end of the year. yes gross. His stuff is in his desk on his desk under his desk. Should be interesting what his locker will look like.
No matter what we have tried we can't seem to get any organization to kick in. And him trying to organize anything stresses him out to where he is overwhelmed. We have at least gotten the leggos in a box and the books for the most part stay in one area of the room.