This sounds like a great Idea.. I would be interested in doing this race. Memorial Day is good timing, water temps Mid-high 60's and usually good breeze.
I've done a bunch of Annapolis-Hampton races in monohulls, it was a popular race in the late 70's, but it was ,at the time, a mid-summer race, which meant drifter like conditions.

Fish-traps are the biggest concern at night, we go to the Dept. of Nat. Resources and plug them all into the GPS.. The mandatory 'reflectors' they are required to have ,every 100yds, do no good at all unless you have a spotlight..

For Running lights on Nacra 20, we duct tape the bow-flashlight (split green-red lens)on the Spin Pole just behind the jib tack. It does not interfere with the Spin there, and can be seen well. For stern lights, we duct tape two small LED flashlights to outboard end of boom, one being backup..

I hope this race happens..