We went to CSA 11/7-11/14 last year. What do you want to know? The only issue we had was with a late hurricane. Really it wasn't even much of an issue other than I think it might have diverted our flight a little and our travel time to MBJ was 30-45 minutes longer than scheduled. We left Memphis on time but landed 45 minutes late. Otherwise, no problems whatsoever.
We've been going to Negril in early to mid November for the last 7 years or so. Last year was the first time we ever had bad weather due to the effects of the tail end of a tropical storm. It was the first time I've ever needed a sweatshirt, and that was only at night. Its usually very nice in November with low humidity and very little rain. 6 out of 7 ain't bad. Best rates of the year during this time usually make it a bargain.
I wouldn't worry about the weather in November. You do run the risk of a very late hurricane or tropical storm (though NOAA has predicted a slower hurricane season for a variety of reasons this year that I don't understand).
Jamaica isn't like some places in Mexico that I've been where they have a very obvious "dry" and "wet" season, particularly on the north coast. You're going to have some rain no matter when you go, and it's just the luck of the draw whether that's in the form of short, predictable bursts or longer overcast/drizzly periods. The area is quite lush and verdent, and it is, after all, rain that makes everything so green.
We've had our share of both good and not-so-good weather, and while of course we very much hope for bright, clear, blue skies, it's really not a big deal if the weather turns. If it's overcast, you'll still get tan, and it's still warm. If it rains, it's usually not an all-day affair, and you can jump in the hot tub or duck under the bar canopy.
I'll tell you what - if you are at CSS the second week of November and it rains, the drinks are on me (we'll be there from the 6th to the 14th)! Seriously, though, if it does rain, the staff normally breaks out the games, or you can always head back to the room and have more "private" fun.
During our trip it was never what I would call cool. Keep in mind I am coming from Omaha, NE so if you are from South Florida your cool may be much different than my cool. The pool water was fine. The only time we were in the pool was one of our first evenings, after 10pm. It was plenty warm enough and it was awesome hanging out at the pool and in the hot tub when everything else was quiet. The ocean water was also warm. One of the couples we were with had been to Ochi in February and said the water was pretty cool. Not the case with Negril in November.
Seriously, do not worry about the weather. I am certain the temp was never below 70 and every day the high was in the mid 80's. The day we arrived there was a hurricane off the coast and it was rainy and windy on the resort. Our first full day was sunny and warm but REALLY windy. You couldn't even walk on the beach which by the end of the day had washed up to the Beachfront Suites. The walkway along the beach was completely covered and it was truly a huge mess. But it didn't matter. We trotted across the street to the Sports Center and hung out by that pool. There was hardly any wind over there. Watched some college football and had a great time. Come Sunday the staff was out in full force cleaning up the beach. The water was still pretty rough by Negril standards but we were able to be on the beach. To be honest, I never think about the 'bad' weather when I think of our trip because everything else was so great. We went with a group of 7 couples and every one had a fantastic time. So fantastic that we are bringing 11 couples this year for the same exact week. And if they told me the weather was going to be exactly the same as it was last year I wouldn't care. It was but a small part of our overall Couples experience.