Wish I could join you, that can be a fun race.
Wxcasts are useless, prepare for anything from zero to 40 knots and expect to be dead in the water and scorched for a day in the Sound. Lay in extra ice and drinks just in case.
If you round the east end at night...it can be a bitch as the shore lights make the nav lights impossible to see. A plotter or good skills are important.
And never say die! Because as bad as your local wx may be and as bad as you think your position may be--you may be doing better or having fewer problems than anyone else in your class. The ALIR is like a box of CrackerJacks, there's a surprise in every box. And inevitably some beautiful sailing.
Playing currents will be crucial to your progress, no matter how it goes.