Hugs - I know how frustrating it can be when you are in the thick of it, and how worrying it can be later on when you ponder the situation and long term implications.

It sounds like he has trouble in the executive functioning areas. This may or may not be related to ADHD. Generally speaking, the executive functioning skills are an area of cognition that deal with planning, organizing, and executing tasks. Not reasoning or knowledge, but how one uses reasoning and knowledge to get the work done and go about life. As people assume more and more responsibility and initiative, and school life becomes more abstract and less structured, poor executive functioning can play havoc. But, people can learn compensatory strategies and develop the skills they need to be successful.

Is EF and ADHD the same thing? There is a lot of discussion about this. Generally most experts say that one can have EF disorder without ADHD but virtually all individuals with ADHD have some aspect of EF. The two disorders very often come hand in hand. My son has both, and we have found that the combination of medication, highly structured routines and explicit instruction on strategies has yielded pretty good results. But, your example of the teeth brushing is something we see every weekend when he is not on his meds! And, like your son, he is cheerful and ernest about approaching tasks. Medication helps him attend to the strategies he has learned, but medication alone does not teach him the strategies!

Here are some articles that give you more detail about EF and ideas to help:

Executive Functioning: A New Lens to View Your Child http://www.greatschools.org/special...-lens-to-view-your-child.gs?content=1017

Is it Executive Functioning or ADHD disorder? http://www.additudemag.com/adhd/article/7051.html

Executive Functioning Fact Sheet http://www.ldonline.org/article/24880

What is Executive Functioning? http://learningdisabilities.about.com/od/eh/a/executive_funct.htm

Here are two books that I have found very helpful:

No Mind Left Behind by Adam Cox
Late, Lost, and Unprepared by Joyce Cooper-Kahn

A neuropsychologist can evaluate for EF. If you are thinking about ADHD, many physicians will order such testing as part of the diagnosis. Maybe a neuropsychological evaluation would be the first step in understanding what is going on. The testing will also help you sort through HS options. (Generally speaking, a highly structured environment would be best) Good luck.