It would be hard to break even on the cost of TiW if you also had the dining plan. The TiW card cost $150 and you would have to spend $750 just to break even. The TiW card will give you a discount on the alcoholic beverages that are not included in the dining plan, but you would have to be at a restaurant or resort lounge, for it to be included in the TiW discount. The TiW only works at sit down restaurants with the exception of the food courts at the value resorts and PoFQ, and maybe a few counter service restaurants. And any food items that aren't included in the
DDP, like appetizers or soups or salads at a table service restaurant, would be covered by TiW. But it wouldn't be worth it to have both the DDP and TiW.
The best time to get the TiW card is if you plan multiple trips or you are taking a big family group - or both.