You would motor or sail at 7 knots or so of dependable speed over ground in "normal" sea conditions? The front's passing through obviously have a variable shift -- you really want the wind to off your stern quarter (and the course shifts approximately from a NE direction to a NNW direction). The clocking of the wind in normal conditions would tend to shift from west to the NE -- the cycle is often short this time of year.

With our boat, you should be able to take some uncomfortable weather, but with it's speed, that might mean you WILL likely be taking some grungy stuff.

If you only concern is with the time, and you've never been in the ICW -- then you only issue would be the depth. You draw about 6' or so?

I don't know what the depth would be inside this time of year, but if you can do that, with a short crew, I'd take the ICW (if I were you).