Hi Lilgabri03 - I'm the same way re research, constantly thinking about my guests, creating spreadsheets that map out the pros, cons, and price differences etc...so much so i think DF was going to consider taking back the ring (j/lk)! LOL So that I would stop obsessing and bugging him, he suggested we price our top pick hotel/air against the top all-inclusive/air. The hotel/air price/person was only cheaper by <$100 so the all-inclusives we liked won once factoring back in the cost for meals etc... for the guests during their stay.
A friend got married in PR in November and had the sell-out situation happen. She didn't realize a large conference was rolling in the weekend of her wedding so guests who didn't book early had to scramble to find rooms. if you are worried about this, I would check to see if anything conferences are happening around that time and pick a different date.