Unfortunately my boat is out of commission for the summer (again), but I fish around Orcas very regularly. I am fully in support of people not taking their boat on trips that they're uncomfortable with so don't let me talk you into doing something dangerous, but I think you've got plenty of boat to fish up there as long as you keep an eye on the weather.
Running from the Washington Park marina up to anywhere on Orcas is normally a pretty easy trip. You could also tow your boat on the ferry if you wanted--it costs a few bucks but if definitely cheaper than a guide. In my experience the San Juans can be very good fishing, but can also be slow enough that even the most experienced boats get skunked. That being said, it is a wonderful part of the world to screw around in a boat. I always prefer to fish by myself in my own boat up there because if its slow you can just call it early. If you're in your own boat, you'll also be able to explore at your own pace, go to other islands for lunch (or a homemade doughnut at the Blakely Island marina), etc.
It's no secret that the hot spot for salmon up there is the west side of San Juan. There are some other honey holes that occasionally produce, but from August through the end of the year, most people fish out there and for good reason.
