While academics have been okay at home, I'd like him to have developed more independence, responsibility and time to work on organization before entering back into school. I contacted our local public school, not the gifted program, and have had several discussions with the psychologist. She is recommending that we do a very long transition back into school perhaps over 6 months, one hour at a time, so he can adjust.
I think I'd share your concerns with him and set up goals together before he goes back: "Jeffy, I know you want to go to middle school, but I am concerned about your ability to handle the responsibility of keeping track of your own homework, getting to class on time, etc." Then set up goals at home together-- simulate homework (assign things to be done in the afternoon, and turned in a day or two later, and his job to remember and keep track), projects, so HE can see where his strengths and weaknesses lie (and so you have something concrete to point to when you're explaining your concerns/kudos later down the road).
Our school system allows dual enrollment (home/public school) so last year my son attended sixth grade for band and was homeschooled for academics. Could your son go in for maybe two subjects for a semester, then come home for the rest, then add more the next semester, then go fulltime the following year (or skip step 2 if he's doing well)? That kind of transition worked pretty well for us, and would keep the clock-watching to a minimum.
And fwiw, both of mine are back in middle school, and while I'm thrilled we homeschooled for awhile, I'm also glad to see that they're putting the skills I worked on with them to good use in a different setting.
