Beastman,
I live in Sandy now, about 30 miles NE of Canby (after living 30+ years in Eastern Oregon) There are some blacktail opportunities over here, but just one tag and not a guaranteed harvest by any means. Many other states definitely have better hunting than Oregon. But if we are talking specifically an Oregon strategy, if you put in for a controlled hunt every year, you can build up points and eventually draw a tag for a higher quality unit that will be a fun hunt even if you don't get anything. Every year you do not draw, you can get a general season blacktail tag for western Oregon and that can be a fun challenge. Some good opportunities for hunting from tree stands that may be similar to what you are used to. Elk hunting in Oregon can be good, many opportunities. Again, the draw units are the best.
Outside of big game, there are tons of great outdoors things to do in this area. Good duck and goose hunting, plenty of salmon and steelhead opportunities nearby, crabbing and clamming at the coast, several lakes and rivers for boating, some decent pockets of public land on the west side of the state and a lot on the east side for ATVs or camping.
I have found if you shift your expectations a little, there really are alot of opportunities to keep you busy while you build up points for some of the better big game tags.