Good responses you have gotten. I would do the written calender of what he has to do when and have him check it off. Natural consequences are best. If he forgets things maybe he needs to go without but if it causes him a lot of anxiety don't do it. He could be stressed about something that is not conscious. I would not be negative but be very positive. Ask him what he would like for reminders and what will help him remember. I don't know if rewards should be used, that is an individual thing. I also would not put a lot of focus on it except in saying you want to help him remember and what will help. You can tell him you will have more time for him if he doesn't need you to remind him of everything. As for the missing clothes, he has to care enough to look so I would tell him to go looking for his things that are lost and set a positive for everything he returns with. It is important to have him be responsible now for things but very positively. He will be grown before you know it. The clothes thing always got me as I hated them to be without and once I paid for something I expected it to be there. I still can remember the things they lost as kids. My husband is way worse losing everything so do your son's future wife a favor and teach him now about putting tools away and taking care of his things.