First off, we are not homeschoolers but I do afterschool and homeschool all summer. (our last summer was 11 weeks- a long summer!) I completely understand what you mean about progressive learning. I think it's hard for people who are new to homeschool in general, to really understand that learning is going on all the time. Kriston talked me down from my proverbial ledge last spring when we considered homeschooling!
We also tested my son when he was 5 because we were told repeatedly that he had ADHD. According to everyone except his teachers then, he does not. He was just annoyed, bored and anxious from repeatedly getting in trouble.
Tough love first- I think you need to step back and figure out how HE learns best, not what is the easiest way for you to teach. It might be unexpected. My son loves loves the computer. I think it's weird to not do worksheets. I've had to learn to adjust to that! I give him a math worksheet on the computer and he's thrilled. On paper at the table and he's whiny and it's "too hard."
Next, realize that there is value and learning in every adventure. Grinity has good suggestions about visiting a class a year ahead. You can also read "What your ___ grader needs to know" or look at your state standards. I suspect you'll have an eye opening "he knew that two years ago" kind of moment.
For managing the day to day, I also have a social one who does not play alone. Kriston told me my goal for the summer should be getting him to play alone and she was totally right and it seriously CHANGED OUR LIVES! I started by hanging up a "20 things to do when I'm bored" list. I would warn him 30, 15 and 5 min before I had to leave him "alone" for a few minutes. We started with 10 min, worked up to 30. If he can't find something to do, then I'll pick off the list- not all of which is good stuff but it serves as a reminder! We also use audiobooks a lot. He can move, jump, play, fidget or whatever while listening to the story.
Consider finding ways around the ants in the pants problem. Have him sit on an exercise ball at the table to do writing or typing. Do math outside on the swings. Do science at the zoo with a camera etc. Use whatever tools you can to make learning less about "school" and more about stretching his brain.
Wow. this got longer than I meant it to be! Hang in there!
