Don't mean to sound negative, but I think this might be difficult to do totally on the up-and-up

And it would be just like Microsoft to go after license money from someone who is
(a) unemployed
(b) using an ancient version of Windows on older hardware
(c) at least *trying* to do the right thing by having a license of some sort

Still, I'd have trouble recommending Linux for beginners. I just don't think it's there yet in terms of the GUIs and the ease-of-use of the various software packages (even OpenOffice.)