Here is a question for Jon, or anyone who has made the direct passage:
Does the Labrador current make the straight shot from Norfolk (or Cape May) to Block Island slower than a run up the coast, staying closer in, and out?
From Norfolk, is it better to go up to Cape May and then to Block Island, or direct course to Block Island?
Hmmm, I'm not sure the Labrador Current has much effect on that route

I've never noticed it, at any rate...
Tidal currents at the Chesapeake and Delaware Entrances, and across the New York Bight, are gonna be far more influential... If you want to try to plan the trip around catching favorable currents, the big one occurs as you approach Montauk and Block, the amount of flow in and out of Rhode Island Sound and into LI Sound is impressive... If you happen to hit the ebb as you approach Montauk, it can make for some VERY slow going over those last few miles, and the effects can be felt surprisingly far out... (Also, the waters around Montauk can get VERY messy in any wind vs. tide situation, that area can become a real washing machine. I'm always clipped on in that area, many of those guys fishing out of Montauk are shark hunters, after all

) Whenever I'm coming across from the Jersey coast, if by the time I'm abeam of around Shinnecock I realize I'm gonna be hitting it wrong, I'll heave to and get some rest, and wait to catch it right...
From the Chesapeake Entrance, I think it's a tossup whether to stay inshore, or go direct, and the weather at the time would dictate my choice. I don't think there's necessarily a real advantage of one over the other, though the straight shot will likely keep you a bit more clear of much of the inshore fishing and recreational boat traffic between Ocean City and Cape May/Atlantic City - but you can still find plenty of those guys well offshore fishing the canyons, as well... Sometimes you might find more fog along the coast then further out, other times it will be the opposite - so the call can really be a crapshoot, depending on the local weather at any given time.
Perhaps the most important consideration - certainly so for a singlehander - is the fatigue factor. You're crossing about 6 different approach lanes going into Delaware Bay and NY Harbor, you really don't want to be too fatigued by the time you get towards the end of the trip, and the Nantucket-Ambrose approaches... So, all else being equal, I'd probably be more inclined to perhaps make a stop in Cape May, and start again refreshed, and with a better chance of maybe hitting the tide right both leaving the Delaware Entrance, and on catching the flood for the final approach to Montauk...