Yes I am suggesting that, and no it is not a recipe for a really uncomfortable day -- it's a recipe for a less uncomfortable day than what you suggested. He's got enough engine power to buck the current and wind, it'll just slow him down. It just means a longer trip and going into the canal after dark, which isn't an issue the way it's lit. The wind is forecast to build from the west late morning tomorrow and through the afternoon, then gusting to 30 in the evening. It will be a whole lot more uncomfortable if he rides a fair current upwind in a wind-against-current chop in Delaware Bay.

If he wants a really comfortable day my suggestion would be sit tight and wait for a better forecast, maybe by mid-week. Tomorrow he'll have wind-against-current chop until about 1500, then strong headwinds on his port bow but with much less chop, but as he gets further north it'll be on his beam and he can probably sail. Either way it doesn't sound like a comfortable ride.