No hunt is truly wasted if you end up learning something and make some memories. I think your plan is a good one, the only reason I would put a harder to get hunt as your first choice is it will allow you to start building preference points for a future hunt down the road. Who knows where you are going to be as a hunter in 5+ years.
If you spend enough time in a particular area you will start to learn the animal habits, where the feed is located, game trail use, etc. One of the pluses of the 119A hunt that
@SiletzTroutKiller mentioned is that you can use that same tag as your general western Oregon deer tag if you don't get a deer during the week of the High Cascades hunt. Effectively giving you an extra week before general season to hunt the same area.
Another thing you could do is look at setting up a couple of trail cameras. I have one I picked up on sale for about $80. It doesn't take amazing photos, but it certainly gets the job done. It also allows you to see animal activity in an area when you aren't there. You can also lay out a mineral block in the view of your camera. It won't bring new animals into the area, but what it will do is give the camera a longer chance to take photos. This will allow you to not only see what critters are in the area, but to also begin to try and find patterns in their behavior. Things you might want to look for while you are out scouting/hunting:
1. Are the animals/tracks all moving in the same direction?
A lot of times they won't use the same path coming in as they will going out.
2. Beds, bedding and feeding areas.
Is there a constant place that the animals go to every day for food/water/sleep? Or is there enough in the area that they simply mill around at will.
3. Do the animal tracks mix? Are there deer and elk tracks on the same trails or in the same areas? Or are the typically separated?
In my experience deer and elk don't like to use the same areas at the same time. Roosevelt elk tend to be rather territorial and don't like other critters hanging around.
Have you given any thought to a hunting buddy? I know that finding a good one is kind of hard, and you might have one already, but if you can find someone to learn with or from it makes it a little bit easier.
My brother and I are probably going to be getting the 119A hunt this year. Our camp is always open for anyone willing to share a campfire. We are going to be a little bit farther south than where you said you wanted to be though.