What about my second question:
Are you talking about sneaking along the coast ducking into protected anchorages along the way?
I would have a completely different opinion of that than a blue water cruise. In a few rare cases, a small boat can actually be preferable (some long stretches with inlets that are too shallow for large boats). But, some of the hairiest water around is inlets with tidal currents and skirting shore lines means there are always nearby shallows and/or rocks to get blown into in a storm. So, while I would have a different opinion, I have to admit I am not sure what it is. Also, I am not one of the more experienced sailors - this is more thinking out loud and repeating what I have read.
Newport 17 - "Kohanna"
At sea Darwin's hypotheses is the final arbiter of right of way.