I think focusing on one aspect of boat design such as "smallest" or "largest" might not be the best way to look at things. For me it's about finding the right balance.
We're very happy with our 30 footer on the bay, but we're moving to the Keys in three years. With the move will hopefully come more free time than we have now.
That has us asking questions like "how will our new cruising grounds change our sailing?", "will we be spending more time aboard, sail further distances, start doing trips to the islands?".
So we're trying to quantify what is really important to us. Then we'll figure out a budget. From there we'll come up with a list of boats tick most of the boxes.
The most surprising thing for me is I can see cats creeping onto the list.