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Bakoom Portland and Eugene are not commutable, in my opinion, but it depends on how long you want to be in your car. It takes about 45 minutes to get from South Salem to Lake Oswego. Eugene is about 60-70 minutes away.
1. South Salem is probably your best bet. Outdoors are accessed from any city in Oregon. We are surrounded by outdoor stuff. South just has easier access than West.
2. Salem does not have a great nightlife scene or arts scene. We do have those things, but compared to Portland it is just lacking. If nightlife is important to you, then I would consider living in Lake Oswego and commuting down. That way you'd be closer to Portland for a good nightlife scene.
In Salem, I would consider joining the Chemeketans Outdoor Club. I have one friend that does things with them regularly such as rock climbing and mountain climbing. They have all sorts of things going on. There are also a couple of local cycling clubs here, if you road bike.
3. We do have some scuba clubs out here, but I don't scuba so I'm not sure where is good to go. As for the other things...I like rafting down the Santiam River, which is about 30 minutes from Salem. A kayak would probably be better than a canoe on that river, but I still occasionally will see canoes. The McKenzie and Metolius are also great rivers that are about 1 1/2 hours away.
The closest skiing is Mt. Bachelor area in central Oregon. There is Hoo Doo in sisters, the Three Sisters, and Mt. Bachelor. There are some great cross country runs and snow shoeing out there as well.
For hiking...I prefer to hike in the valley areas because I find Central Oregon too dry. Close by hiking we have Silverfalls State Park. It's like 30 minutes away. Then there is Opal Creek area, Bull of the Woods, Chimney Peak...there is a bunch of good hiking in the Mt. Jefferson (most locals call the mountain Jeff) Wilderness. If you want to do more of a weekend getaway, there is some great hiking in the Mt. Hood Wilderness. Trillium Lake, the hike to Paradise are really great.
Then...on the coast Cascade Head has some nice views. There was also a trail I loved in Manzanita that had a breathtaking view at the top. The name of the trail is escaping me at this point though...
So...I would focus less on access to outdoors (because you are surrounded by it) and focus more on your daily lifestyle and that will help to determine where you live.
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