It all depends on what you are looking for. I chose September because the hotel was extremely inexpensive during this time (after the low rate, discounts, coupons, my rate was less than $70/night and included the full breakfast buffet for 2 adults). It is the off season, so the crowds are much less, we found that there were numerous shopping sales going on and discounts for food so that decreases the costs even more.

The weather was great and yes, it is during hurricane season. But most airlines and hotels will work with you on either cancelling the trip or changing the dates should a hurricane hit during your trip. (Unless you are planning on a more than 1 week trip, you should have a pretty good idea if a hurricane is about to hit the island before you head there.)

If you like crowds, higher prices, less chance at an upgrade, then definitely the winter months are for you.