SD - a hint; its a monohull (although I did consider cats) and its listed on Yachtworld
Jeff - thanks, I have always enjoyed your knowledgeable responses.
Ed - there certainly where (are?) compromises as each boat has its design purpose. I have a special consideration in that I need a shoal draft, but that still left hundreds of possibilities. I knew I would be doing a lot of day sailing. So, I spoke with local sailing schools, instructors, neighbors and friends I know that sail in the area to try to get a feeling for the sailing conditions (as I am new to the area) and also for what size, displacement and type of boat to get that is best suited for the conditions.
I also knew to get the admiral to go along it would need to be a comfy boat; in really good condition, big enough that we could take it on short (or longer) trips, but small enough that I could single handle the boat much of the time.
Being old(er) I did not want to be in the boat buying and selling business, so I was looking for the one boat that would satisfy the above and my wants. I am a lazy sailor (did I tell you that I was old already?) and so it needed to be easy to sail. I am (was, I guess always will be) an engineer so function usually wins out over form, but I knew I needed to like to look at the boat. I want to feel proud owning it. However, I really don't care what so much what other people think.
So, I made spreadsheets of boat specifications, and compared their PHRF ratings (whatever those are) to rank boats that I was considering. I also needed to establish a budget and price range. So I included boats that I might not buy but that there were enough of them to get a good feeling for the price distribution over age and condition. I can go into more detail, but its not really worth it. Because in the end I found a boat we both liked and that was that. But the process did make me comfortable with my (our) decision as I had to come to grips with all these factors.
I looked at smaller boats (<30 ft) and mid size boats (<36 ft). I decided, based on good input from the community here, that I should get a larger size boat as they are no harder to 'learn to sail' than a smaller boat with todays modern equipment.
In the end I did compromise in some areas, but tried to stay true to the main purpose of the boat, to enjoy sailing.