When I first started visiting Jamaica, it was always in September. The classic tropical beautiful mornings and afternoon rains before sunset seemed like the perfect combination. The hottest month on the west side of the island is July, east side of the island is August, so September is the beginning of the cooling off heading into our busy season.
I always enjoyed the slow pace of September. After living here, I have seen extremely hot days in winter as well as cool days in the summer. Just a few short days ago, we didn't even hit 30c during the day.
Weather is weather, it will be whatever it is at the moment.