Interesting to see more choice in this size range of boats. Will a 21ft shrimper be towable? The shrimpers have always been rather expensive IMO.
Dennis, I think the Cape Henry is a very attractive prospect.
I did see a Drascombe Drifter 22 and really liked the look of that (though not a trailer sailer)- twin keels gives a lot more space in the cabin and the extra length makes it feel a lot more substantial. Only 2 berths though.
In the end, if I was looking to trade up, then I would be looking for a bigger step in size, in order to gain the benefit of more internal space. However, living in the midlands as I do, a trailer sailer will suit me for the forseeable future (although I'm not looking very far ahead