Paying for each meal out of pocket isnt any more difficult than paying with a prepaid dining plan. It's in fact easier to pay out of pocket because you don't have to make sure what you're ordering qualifies under the dining plan. We paid with our Magic Band.
We've done one trip with a dining plan, and one trip without. We truly enjoyed paying out of pocket more because we ordered what we actually wanted in the moment instead of being required to order certain things. Some days we ordered several appetizers and split them, some days we shared a meal, and some days we each ordered an entree and enjoyed several alcoholic beverages. We also paid out of pocket for the refillable mugs since we stayed 9 nights and enjoyed a soda or hot cocoa in the evening while relaxing poolside or on our balcony. On really hot days I sometimes opted for Kid's meals for lunch because a heavy meal was not appetizing.
When we had the dining plan, we never wanted an entree plus snack/dessert plus beverage at each meal. We mostly drink water in the parks due to all of the walking so we were paying in advance to just get water, and dessert plus an entree was just too much at once. We preferred to space out things like that...eat lunch somewhere, then a couple of hours later get ice cream, etc. We declined a lot of desserts and felt very overstuffed a lot of the trip.