greetings -
i can't comment on conditions, as am living in Colorado, but i lived in Portland for over 15 years and have climbed extensively on Mt Hood.
> the south side is a walk up and is usually crowded. you can bypass a lot of the traffic by climbing the "west crater rim" route if you want to stay on the south side of the mountain. it is a good alternative, sees a lot less traffic.
regarding north side or west side routes
> "castle crags route is a lot of fun. west face, gully climbing above the reid glacier. you finish on the west crater rim and walk it to the summit. moderate slopes of 45 degrees. conditions vary.... you can start and finish on the south side at timberline lodge for this route. i have done this without roping up. good solo route if you have the skills... no glacier travel required if you cut into the headwall early after crossing illumination saddle.
> sandy glacier headwall is also a great moderate climb that can be done from the south side approach. a longer approach as you need to cross the reid glacier and go around hokum ridge, but great climbing. descend the south side... roping up for glacier travel is probably a must for this route. moderate slopes of up to about 5o degrees, conditions vary...
> north side routes - you can access these in a couple ways. snow pack dependent. from th old cooper spur ski area, you can ski up to the north facing routes. climbing the sunshine route, cooper spur or the elliot headwall. all are great climbs. i suggest partnering up and setting up a shuttle, leaving a car at timberline lodge, descending the south side after the climbing and driving back to the start to retrieve the second car. the claims on the north side actually get sun in the afternoon and can make for treacherous descents. that is when people usually get into trouble on those routes.
>last option from me -
i have done the elliot headwall form the south side by climbing the south side route, then descend the upper part of the sandy glacier headwall route, which is to the west, then traverse the sunshine route into the elliot headwall and climb back up over the top, descending the south side to timberline. it is a long day, but super fun if you are fit and get an early start to put yourself into position for the elliot headwall..
one note on the elliot headwall, there can be good ice climbing at the top of the route, but it is totally dependent on conditions. there is a climb around if the ice is out of shape, that will lead you to the top, moving left and merging with the top of cooper spur.
also - this can be done without a partner. you are pretty much above all of the crevasse danger, staying above the bergschrunds of sandy glacier, sunshine route and elliot. i with with a partner roping up for the climbing, not for glacier travel.
lastly - it has been awhile... so take all of this with a grain of salt and do your homework on the route selection, etc...
that is all i got.
good luck...