Kevin,
All the routes on the mountain can be climbed in
the winter, in stable conditions, but all of the
routes with easterly facing aspects are going to
be the most avi-prone(NE,E&SE); this because most
of the weather patterns come from the west. This
would then make your westerly facing routes a bit
safer choice(Cooper Spur is also the route most
people fall on and deaths occur!). I personaly
would recommend the Reid Glacier Headwall(many
possible variations!) or perhaps Cathedral Ridge
(early season variation) as both are steep enough
to shed new snow quickly and subsequently make for more interesting climbing. Try picking up a copy of Jeff Thomas 'Oregon High'; it has all of
the routes on Mt. Hood, as well as the rest of
Oregon's Cascades. Talk to ya labia!