Milo - Re voluntary tutoring
Until recently I worked at one of these centres dealing with the people that you describe:
The problem is not the the Tutors are all Dos 3.3 users - it's that they are under pressure to deliver a proscribed program in a limited period of time.
The proscribed program(s) bears no resemblance in reality to the real world of Win 7 or real world "home computing" these days.
The technology is hostile to many people - its about lifetime exposure to the technology - Come Win 8 and I'm with them - just you wait until Elliptic curve cryptography hits the shelves.
Now explain that to a seventy year old.
CAT III