Re: Sailboat under $5000 for Puget Sound
You can check the Second Wave stock at secondwave.cc. They do negotiate if pricing seems high and they have a lot of stock, I recently got a Fortress FX-18 (which I'm using as my secondary anchor) price knocked down $25 just by asking.
There is also a used boat supply place in Poulsbo, another good place to try anchoring and a nice little town. It's much smaller than Second Wave, but still pretty nice.
You are correct that there isn't much along the Whidbey side. Sail down it and you'll see why. It is mostly cliffs right into the water.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior