It is hard to spend more money paying cash than you would spend on the dining plan. The dining plan is priced figuring that you order the most expensive things and eat every entitlement they have given you. You don't have to look at the prices. Cover them up and order whatever. You will most likely still pay less than the dining plan.
It's difficult but not really that difficult if you follow the rules. We kept a spreadsheet and found the easiest way to get your money's worth...
1. Everyone uses their mugs in the morning, and at night.
2. Get a mimosa with your breakfast.
3. No signature meals, 2 credits is generally more expensive than paying cash.
4. I don't care if you don't drink alcohol, you're having alcohol with your lunch.
5. Snacks should be above $5. Preferably $7+
6. Yes that grapefruit beer will go wonderfully with your dinner.
7. Dinner? Garden grill. Why? Chip and Dale. The kids don't know it? We'll download it, they can watch it while we walk. We're only doing character meals.
8. Yes, I asked. We're allowed to substitute the alcoholic smoothie as our drink.
9. SO: "I can't decide between the Steak or the Chicken." Me: "Which costs more?"
10. Just grab that alcoholic milkshilk for desert. I've got a bottle of water and we'll deal with AA later if we have to.
Granted that approach does not lead to a peace of mind/stress free eating either.