Captained my first charter with the Moorings in the BVI last March and the weather was fantastic.
My GF and I had a 39' Bene to ourselves and were welcomed to 20+ knts right out of the slip, was quite a surprise. The wind challenged us the entire trip and I was happy to see it actually. There was only one calm day, but sunny skies throughout except for a few stormy passer bys.
We had only one gale that interfered with plans, mainly Anegada. I just wasn't comfortable navigating the approach with an overcast and a mean blow pushing us on our aft quarter. So I scrapped the passage there and went elsewhere.
I don't know if it was the time of year or not, but as a kid chartering there with family many times I never remembered the weather being that active. We always went in late December though.
My suggestion would be to bookmark a couple of the local weather forecasting sites and pay close attention to them along with the WX every morning. Be mindful that the only local Radar is PR
's. It didn't represent a lot of what we saw accurately at all. At the time there were no functioning offshore Weather Buoys either.
I would have all my weather sites tabbed in my browser and just open the whole bunch at once to suck as much Wifi as possible, which we found very difficult to get while moooring.
As for crowds, it was packed. However, my observation is a bit tained as the last time I had been there was when some of the islands were just getting power lines and chartering was kind of new to the scene. No cruise ships either. So I was of course a bit devastated when I saw how packed some of the places were that I ventured as a kid without seeing a soul.
It was a great trip though and we met a lot of great people.