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A few years back (late '90s, maybe), a retired CG Captain did this trip in his Bayfield 25, solo. He recounted the trip, in serial format, in Messing About in Boats. It was a good read.
He was able to transit several of the many small inlets along the Atlantic coast of Delmarva, south of Ocean City. He emphasized that charts were unreliable in this area due to constantly shifting shoals. He made a point of contacting the local Coast Guard stations to get the very latest local knowledge before entering an inlet. In some cases, they came out and showed him the way in (possibly because of his CG connections).
One of the things that sticks in my memory from that account was the trouble he had with bugs/flies/mosquitoes. I think he set-off in mid-May to try to avoid the worst of them, but they were still pretty bad.
With adequate prep and precautions, I would think the improved sailing ability of your Merit would be an advantage, if not quite as comfortable as the Bayfield 25.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT