We really love the dining plan. As someone who is constantly pinching pennies and trying to get myself the cheapest thing on every menu, I love not having to feel guilty for wanting the most expensive item. I love not really having to think about it. On the other hand, I sometimes feel pressure to get the most expensive thing, over what I want, to make sure I'm getting my money's worth. The thing is, after looking at every menu I think we'd want to dine at and doing my own calculations, AND using a dining plan calculator, we end up saving money paying out of pocket, about 50-150$ or so. The penny pincher in me wants to save that 50-150, but also wants to be carefree at Disney and tell them to keep the steaks coming and to not look at prices. Is the convenience worth that 50-150? I'm going to over think it all either way, but is there a good middle ground? Do I want to save money or do I want convenience? Help!!