@Holley
Well... the person happens to be my girlfriend. And despite my warnings and insistence that Amigas aren't for everyone, she's hungry to learn what she can. Unfortunately, her hunger isn't self-sustaining like mine was back when I knew nothing. When I'd get stuck, I'd dig in and wring the answer out. When she runs into trouble, she stops and won't go any further until I've written out 47 pages of notes with arrows and captions detailing what the next step is.
@Ilwrath
I think you've hit the nail on the head. I haven't done much in the way of building confidence. So far my approach has been 1) pump out information and instruction and 2) experience shock and horror when my elaborately presented information and instruction isn't immediately absorbed. That's where I can certainly do better.
In some ways, I think starting out with a system like my first A500, a system which had plenty of appeal at the time but didn't automate much of anything, and relied on floppies and user know-how to get anything done taught me that if I was going to get anywhere, I had to grab the bull by the horns and just dive in. Nowadays, with Windows being fully functional and productive right after installation, people don't have the same prerequisites. In a way that's good because people can focus more on the software they're using. But it's also not so good because when things go wrong, they're completely lost until the machine comes back from the shop.
Another simple problem that cropped up today was a misunderstanding that the location of a file on a hard drive determines the type of the file, what can load it and what can't. Saving a jpg in with other pagestream documents and then loading that jpg as a pagestream document can cause all kinds of funky stuff to happen. Windows is a little smarter about it than the Amiga is, but it still helps to have a grasp on what's really going on there.
So here's the question: do you think it's worthwhile to set up a completely out-of-the-box A500, show a few things that'll get the learning process started and let nature take its course? She wants to learn, and I think the things she's wanting to know aren't retained as well on a fully-configured system. I'm thinking if she uses a system that doesn't do anything Windows users (or halfway decently configured A4000 Tower users) take for granted, and makes some progress with it, she'll come away with a better understanding of what makes computers tick in general. Does this make any sense?
I'm afraid though that having used Windows as long as she has, she's kind of spoiled in what she expects computers to do for her, which is going to make it more difficult for her to grasp some of the pieces that'll put things in better perspective.