Thanks all for the replies, special thanks to Jeff & Jon yours were particularly helpful and objective.
I think I am a bit nostalgic about the Westsail because of so many web sites I have read that were linked from the original I stumbled upon. These people really appear to enjoy their boats.
I think you are correct that most people do like their choice of boat and justify it however possible. Heck, I justified owning a Pinto once
and there are not too many IHATEMYBOAT.com web sites out there. Actually the URL is available I checked.
Surprisingly, no one made any suggestions on an actual boat or brand. I originally wanted to stay away from ‘production’ boats but now I am thinking of a coastal cruiser that will hold its value so I can learn on it and see if it is the life style we want. I will probably charter a few times after the 101-104 course and have a captain along the first few times. Chartering seems to be a way to test a few boats and get it right. 35 ft is about the max I need.
Crewing may be an option but it is probably difficult to find someone who wants a husband & wife team that has almost no sailing experience. Being gainfully unemployed I may hang around yacht clubs and offer help as crew on day sailing excursions.