Jesse and I are at our wits end trying to help Jackson maintain a clean room. We have the same conversation at least twice a week about how bad his room is AGAIN, and we ultimately clean it for him. It's gotten so bad that he's been leaving his dirty clothes on the floor wherever he took them off (his room, the bathroom, our room, etc). I absolutely refused to pick up his clothes so Jackson's clothes were never washed last week. He never went without clean clothes; he just didn't have his favorite pajamas and clothes.
We try to require him to clean it as he makes a mess, or even just before bed each night. The problem is Jackson is very imaginative and spends a lot of time playing in his room with everything at once. He invites his siblings to play in his room with him, which results in an even bigger mess. The other challenging thing is Jackson is notorious for multiple wardrobe changes throughout the day. We help him clean his room on the weekends before Jesse vacuums upstairs. During the week, it becomes unmanageable for him.
Our latest attempt involves bribery. Jesse and I came up with a checklist that Jackson has to complete each night before bed. If he cleans the five areas of his room, he gets a sticker each night before bed. If he gets all seven stickers, we'll reward him each weekend with something small (trip to SweetFrog, blind bag, etc). To be honest, he gets those things anyway. Now he just has to work for them.
Here is a copy of what we're printing each week. I took pictures of the five biggest areas in his room, labeled the photos, and created a Word document to help him visually sort out what he needs to do. We're been trying to teach him to focus on one thing, such as put all your books away before anything else, then pick up any clothes.
I'm not proud of raising a slob or resorting to bribery, but I hope this helps teach Jackson how to maintain a clean room. I'll update in a few weeks with our success rate.