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Originally Posted by TheAlpineOracle
These all-inclusive resorts as all give and take. The beaches are the best in Cuba and the Dominican Republic and they are probably the safest (Cuba being the most safe), but the food is straight thrash and generally there aren't direct flights from Calgary so you have to waste a day in Toronto. Mexico generally has the nicest resort complexes and the best food, but it's getting sketchy from a safety perspective and the beaches outside of the Mayan Riviera are hit and miss (even Mayan is hit and miss now with their sea weed problem). I think most people have taken Jamaica off their list altogether because of safety reason. Barbados/Turks & Caicos/St. Lucia are generally the best, but they are significantly more money so I don't even know if you group them with the others. Might as well go to Hawaii for the money you pay to go there.
To me, what it comes down to his how good of resort you can get for the lowest price and the best travel schedule. Get the nicest resort you can with a direct flight for the lowest price. Experience will be the same no matter where you go.
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You can definitely find resorts with food that is of much better quality than others.
But you are right in that watching for deals is the best way as they always come along. We went to a very nice resort in Dominican last year and paid about $1000 less than what it normally cost by watching for a deal (we also booked very far in advance). Place was amazing and had great food.