Great info so far!
We trailer the boat to Orcas. Research the ferry cost, it's not cheap and I highly recommend using the ferry reservation system. If you're going, better get reservations soon, the good houses book up fast. The islands are not very friendly to trailer boats. Only one public launch on Orcas and it's on the east side of the island. I've launched at every ramp (6 that I know of) on the island. Once you decide (if you go to Orcas) on what part of the island your going to I can help with which ramp. They all have their nuances.
Another factor is, if you're going to leave your boat in the water (we always do) then you either need a house that has a mooring buoy, bring your own or get a slip in a marina. If you get a slip then you need to contend with traveling back and forth to the marina and parking. A buoy then you need to get back and forth from the boat to the house and some areas have a very difficult shoreline for this.
When you research the houses on-line, most do not consider that you're bringing a boat and don't give much information that would be relevant to someone with a 30 ft long trailer that may need to be turned around. Last year we pulled down the driveway of our rental home (first time to this one) and there was no way I could turn around or back up. Had to disconnect the boat and spin it in the driveway.
Fishing, other than salmon, we have given up on fishing in WA. We now get our Canadian license (online) and head across the border to catch a meal. If you do this, you need to stay on the north side of Orcas, or on San Juan island to make the distances manageable.
We love the islands. The pace is slow and most of the people are great. You routinely see people hitchhiking to where they need to go. Everyone is on "Island Time" so embrace it, slow down and relax.
There's lots to see and we routinely spend about half of the daylight hours on the boat, cruising the islands, hiking and fishing. Hope this helps!
Highly recommend http://orcashomes.com/vacationrentals/
for the house. Karen is the best!