First of all Anacortes is a great location, I sail from Point Roberts, second of all you say you are close to the water? How close? Can you leave the mast up and just tow over to the ramp without worry of overhead wires/obstructions? I used to trailer and now slip, it is expensive but the Missus insists on it. The only difference between trailering and slipping is the mast raising itself, all the other stuff is done wether you trailer or slip, still takes us 1/2 an hour to get everything ready to get under way from a slip. The slip just provides us a destination to visit/hang out when we wish.
We also bought new, next time if ever it will be used. I had to aquire every little extra at a great cost and do not wish to do it again.
I have a MacGregor 26M and it gets us all over the San Juans easily and comfortably, it is a great first/starter boat to learn in and has easy and good resale potential.
We have Macgregor regattas in Blaine every year if you wish to race in the same class, but do not be too quick to assume you won't like a powersailer, they are plenty of fun and the Macgregor has way more interior space than anything else in the 26' range. Also do not assume you will need a better performer as a sailboat, learn to sail first then decide, the hybrid powersailer motors at twice the speed of a standard sailboat and when you start to explore the San Juans you will motor exclusively, the winds, weather, currents and tides are not always in your favour so don't think you are going to sail everywhere. You will only daysail, as we do, any travel to the islands will entail motoring unti you arrive at your destination with a dinghy in tow. When I first looked at the MacGregor my impression was that it is not a real sailboat and I turned my nose up at it. Now after six seasons of sailing it I have come to like it a lot and appreciate the hybrid qualities of it. The Mac is very well suited to venue you are sailing in and there are plenty used ones available in your area, check them out with the missus.