I've seen posts by those who tried it for quite a long time and Dkids didn't thrive and really needed more structure. I like the idea of Bravewriter for instance that emphasizes narration, copywork, dictation once/twice per week at this age but I'd be fooling myself to think DS would voluntarily do those activities.
If my son gets to a point where I think he needs more structure, then we will change what we are doing. It won't be the first time. Right now, we are on call to provide respite care for my mother and structure isn't really even possible.
If my son doesn't start writing more on his own in a few years, I might have him try Bravewriter, but for now the only thing I really make him do is math and sometimes handwriting. I wish I could just get him to record his thoughts, especially the funny ones, in a daily journal.
One thing that he is doing on his own and even enjoying it is playing SAT Coach on his Nintendo DS. He wants to improve his math scores on this game. He also has an ACT prep book that he can look through to see what he needs to work on. He wants to be able to take college classes early and he is working toward this goal.
