Pineapples are climacteric fruit aka fruit that ripen with an burst of ethylene production that triggers the ripening process.
Breeding for a decrease in ethylene production delays or stops the ripening process. This allows for a buildup of sugars in the fruit. 50-100% more in some species. It also increase the shelf-life so they stay firmer longer.
So the extra sweet label and the darker green color of these fruit indicate they are a variety that was bred to down-regulate the ethylene burst. Dole is attempting to capitalize on their newer variety (poorly).
Commercially grown in an appropriate climate, an individual pineapple plant of the species typically grown for mass consumption can mature and fruit within 2 - 3 years. It depends on a lot of factors, though.
I don’t know about these but premium fruit can be substantially better. Seeded varieties of grapes are like little sweets. I believed grapes were bland and boring till I tried extra special ones. This got me trying lots of premium fruit in my supermarket.
Strawberries and raspberries are better, but don’t match home grown. Apples are very variety dependent. White fleshed necterains are significantly better than most peaches. Extra special melons seem to have a much smaller window of availability but are worth getting when they’re available, so much better than the usual watery disappointment.
I think premium fruit doesn’t have much social currency or ‘clout’. It isn’t branded and no one knows your having anything different. The only difference is the taste. So it’s not very sustainable for supermarkets to stock and sell more expensive fruit if it doesn’t have a market. So I would try them, especially if you haven’t enjoyed that fruit in the past.
As far as the price. If you really stop to think about the about of effort cultivating and shipping that fruit to you. The price is redicously cheap. Try growing a pineapple, and then take it thousands of miles away.