The short story: You won't find a better place, location, and price on Orcas Island. (by the way they recently changed their name to salish seaside escapes and you should check groupon and living social, they frequently have deals). This is one of the few places where you have public access to sunsets, views of Mt. Baker and the coastal mountains of British Columbia, a pretty good beach, and you are close to town. They have several different housing options. I have stayed in the salmon shoal and the seal point. These are the larger homes and they have smaller options as well. I stayed at the Seal Point about 7 years ago (July 2007) and at the time it was a bit old and in need of some updates, but still very nice and comfortable. Certainly clean and nice. It appears they have updated the home a little bit. I remember there being a "bedroom" that isn't really separated by full walls from the living room that was a bit disappointing. More recently we stayed at the Salmon Shoal, which is also nice. It could be updated, but it's very functional. What is nice is that there is a very separate living space under the house essentially in the basement. It's perfect for a family like mine where I have a 2 year old child, so my wife and I could have our own space and could put our son to bed down stairs, but the rest of the house is shared with our travel companions and allowed us to hang out together after putting my son to bed. The house is PACKED with random stuff that is sort of fun (a lot of it bear themed art and nick-nacks). The kitchen was very functional, the grill on the balcony was difficult and of poor quality, and the hot tub was very nice. The kitchen was well stocked with dishes and all the pots/pans/utensils that you'd need. The dish washer and washer/dryer are nice and function well. You definitely get a fully functioning house here. The yard is beautiful with gorgeous flowers and a little bit difficult access to the water with crawling over slippery boulders to the water (at low tide), but once you are there, there are interesting tide pools with star fish, sea anemonies, and other interesting tidal pool life. We took the patio furniture down on the lawn to watch the spectacular sunset each evening. At high tide there is basically no beach and water access as the water comes right up to the house. While I don't know for sure, I think that during the winter (probably October to March) you probably don't get a direct view of the sunset, at the same time, it's not likely the weather will cooperate to show you a sunset anyway. Also because of tide flucuations, you might not get any water access during the transitional parts of the year because of tide related issues (probably around october and march). This is a family owned business and they are very friendly and easy to work with.
The house is on a very much not busy road which is nice for a stroll down to the public beach down the road, and you could walk to town if you wanted. It's about 1.5 miles to town, and fairly flat, so it could make a very nice walk before and after dinner. The new-ish brewery is a similar walk.
I highly suggest you visit the San Juan islands some time in your travels and Orcas Island is my favorite and this is clearly the best place to stay on the Island all things considered.