I see debian getting a foothold at the bottom before the
top.
freegeek.org (where I have done some volunteering, and plan
to do more) has already given away thousands of refurbished computers
with debian installed on them. Admittedly many of the people do
the volunteer work to get their free computer, and then go, and install
a M$ OS on it, but as debian improves the number of people sticking
with it increases, and the evidence is in the number of people calling
the tech support line. (only the pre installed debian is
supported). Free geek hasn't been around all that long, but
already people in other cities have copied the model. So if you
want to really promote debian this is a good way. There are other
examples like the cheapo PC's that Fry's sells with Linspire, and HP
selling machines over seas with Ubuntu pre installed, but those aren't
quite debian.