We are going in November.
Maybe it is a Zen thing. The low puffy clouds, beautiful beaches and stunning sunrises really are worth it. We did not like missing our Spring trip at all and going there will make up for it as best we can and the imminent darkness and cold of late fall and winter here will seem less intolerable. We will exercise precautions going to SXM just like we would when staying here in MA. Sure, there will be limitations but we are okay with that.
Not waiting for travel conditions to be absolutely perfect. In two years we will look back and say glad we did.