Everything that you say sounds very familiar
In my case, I have just about zero available sky to the north and west, due to trees. I have a gap in the trees to the south where I can catch something for about an hour. And I have about a 30 degree horizon in the east.
I have a better situation with light pollution, since most of my LP is to the southwest, which is largely blocked by trees. I also live in a rural area, where none of my neighbors' lights can reach my back yard directly. On a dry, moonless night, I can actually get pretty decent RGB exposures by catching an object when it rises above the tree line in the east, and then following it until it drops below the tree line in the west. For being as close in as we are to the Seattle area, I am not complaining.
I'm familiar with Gig Harbor. I would think that you'd have huge light pollution off to the west, but I would guess that your southern sky is better than mine, and there's not a whole lot of civilization to your west (trees notwithstanding).
I do attend Oregon Star Party each year. I also attend Table Mountain on any year when it doesn't conflict with Oregon (which is not very often any more). And I attend Golden State Star Party when it doesn't conflict with Table Mountain. I also fit in a few of the smaller events in the Pacific Northwest, like Camp Delany, Pixieland and Brothers. This is the last year for Pixieland, and Brothers is revamping and moving near Prineville, OR. There's a new event that started last year called Logan Valley Star Party in northeast Oregon. I'm thinking of trying that one this year, too.
It helps that I have a motorhome for longer stays (I'm at the OSP site for around 2 weeks each year), and have a truck camper for short stays, like Camp Delany - and even Golden State, which is typically 4 nights.
What I've found that really increases my productivity is automation. I keep an imaging rig set up almost all the time on my property, so I can take advantages of intermittent clear nights (we might have one tonight). I use SkyTools 4 to plan the objects I want to image. I have a big list of objects, and it tells me which ones are favorable on any given night and location. It even considers the tree line at my home. That way, I never get stuck with what-am-I-going-to-image-tonight-itis.
The one suggestion that I might make is that, based on everything you just said, you should be thinking "smaller" and not just "simpler". I think that you would benefit from a setup that you could reasonably pack in your car and get out a ways. I would imagine that there are some nicely dark places on the Olympic Peninsula that are far more accessible to you, than they would be to me.
At the low end of this, you could do some nice wide field work with something as simple as an AVX, with an 80mm F/6 triplet and a one-shot-color CMOS camera. Set up the imaging package with an OAG and a mini guide camera. You could keep the scope, OAG, camera and guide camera assembled all the time and move them around as a single unit. If you get an imaging camera with a built-in USB hub, then you would just need one USB cable and one power cable from a laptop to the telescope. It would take just a few minutes to set up and polar align the AVX, and you could run the whole thing with a cheap laptop.
If you want to image with narrower fields, then you could go with something like and EdgeHD 8 scope with the F/7 reducer. The camera package would the the same as I just described, but you'd need to step up the mount. I have heard that a CEM60 is pretty light, and it should easily carry an EdgeHD 8, without breaking a sweat. With a bigger budget, I would consider a Mach1 (or the new Mach2, but it's going to be less portable than the Mach1 for a few reasons).