I have no good advice regarding perfectionism, as I suffer from it and DS7 suffers even more than I.
However, one thing that you might want to look at is a book called "Drawing on the Right Side of the Brain". It is a pretty simple course that can vastly improve art skills in just about anyone. I recently checked it out at the library in the hopes of getting DS7 interested in trying it, but we just didn't have time right now. I did some of it myself many years ago, and it's quite interesting. It's about changing the way you see things to make it easier to get them down on paper. I loved the "negative spaces" part in particular--you try drawing a chair, like a wooden kitchen chair for example, and normally they give you fits because of the perspective of the legs; then you draw the same chair by not drawing the actual chair, but the spaces around it. It's amazing to find that you can do a good rendering of anything requiring perspective that way--by drawing the "not-chair", so to speak.
Anyway, I sure know how your guy feels, because I've always hated that things don't come out the way they look in my head; perhaps I should have done more of the course in the book.
