Yeah, you could come up Barbur/99 up to Hall Blvd. I believe Hall has a bike lane all the way up to the Washington Square area. I've ridden Hall before but I would turn off before reaching Washington Square. Be aware though that you'll be trading one climb for another. If you come Barbur/99 you'll have to climb Capital Hill. I've never ridden Sylvan so I can't compare the two but Capital can be a challenge.
You might want to stop by a bike shop (Bike Gallery, River City) and pick up a Bike There Map (~$6). It'll show you where the bike lanes are and auto traffic levels. It'll help you plan your route.