Sharpies are a tough call in many ways. Traditional New haven Sharpies and their many derivatives were very tricky boats to sail. They carried huge sail plans so that they could sail in the light winds of Long Island Sound and were unballasted except for thier catch. In order to sail well sharpies had to be quite narrow. Beamy or heavy sharpies really were miserable boats in all ways. They depended on flexing (or breaking) of thier very light, unstayed rigs to depower in a gust. If you read accounts of the New Haven Oystering fleet, these boats would fairly routinely capsize or loose rigs.
In a chop these boats were known to really pound and so windward performance was never optomized because a real beat would be horribly bone jarring. Bearing off a little and heeled over the pounding was a bit less. With thier flat bottoms and huge rigs these boats were very fast (for their day) on a broad reach or a run.
Commodore Monroe really made huge gains in improving the design of the sharpie to make them more suitable for offshore work. The legendary ''Egret'' was a very interesting exercise in improving the seaworthiness of a sharpie. She was a ballasted double ender which Monroe referred to as a ''sharpie lifeboat''. Her expoits were legendary, sailing out through surf to meet ships, she performed wonderfully and many copies of the the conjectured design of Egret have been built. (There is little beyond a couple blurry photgraphs to record what this wonderful little boat looked like) Egrit worked because she was constructed with very light materials above the waterline(juniper cedar which is a southern form of white cedar that bears no actual relation to juniper and which is nearly extinct), was very heavily ballasted (partially with her cypress bottom) and was fully decked. In her day she was a real wonder.
The other thing that happens about that time was the development of the Nonpariel Sharpie. This happens at the western end of Long Island Sound and spreads quickly. Originally vee bottomed they get to be a molded shape. This molded shape corrects some of the pounding problems of prior flat bottom sharpies. Again these are heavily ballasted boats and were much better suited to yachts and being offshore than the flat bottom boats. The problem with the Nonpariel sharpies is that they gave up one of the really big advantages of the original flat bottom sharpies which was ease and low cost of construction. They also went to stayed rigs which really was at odds with the somewhat tender nature of a well designed sharpie.
Again, Commodore Monroe came up with a variation of the nonpareil sharpie that was a wonder of its day. But in my mind it is very far afield of the original sharpie concept and while a good boat for its era, really should be seen as something other than a sharpie in my mind.
The Meadowlark is a variation on the Nonpariels. It was L. Francis''s attempt to blend a diverse collection of ideas into a single boat. The hull is loosely based on the nonpariels and the rig and leeboards were based on traditional Dutch watercraft. They were designed for a purpose that really did not include offshore passages.
When you talk about sharpies as offshore boats there are some fundamental problems in the type. Sharpies by their very definition were heavily dependent on form stability. They also have pretty high wetted surface to displacement and pretty high wetted surface to stabilty numbers. This means that they are not exceptionally easily driven hulls (although their narrow beam helps improve the ease with which they are driven). To overcome this compartively large drag, you need to carry a big rig and carrying a big rig with minimal stability is not a great set up for offshore work. The other thing about form stability is that it results in a very quick motion and in general these high form stability boats loose positive righting moments somewhere down around 90 to 100 degrees of heel which is not considered adequate for offshore work,
If you were to evolve a sharpie for offshore work they would look very much like a modern IMS typeform. The flat bottom has been modeled to have fine vee''d bow to reduce pounding. The hull sections are carefully modeled to reduce wetted surface. A fractional rig that can be quickly depowered has become the norm. A deep keel with a large portion of the boats weight in a bulb has been added to dampen the quick motion and allow the boat to stand to its rig, BUT it is no longer a shoal draft boat.