To make a long story short, it's cheaper for me and my better half. Don't want to read, skip straight to bottom for the breakdown.
One of the things she mentioned to me is, "I'll go on all the rides you want as long as we get to dine in style." So then I had the dilemma of deciding whether to use cash or the dining plan for meals. So we went through every UP TO DATE menu of the restaurants we made reservations at, and picked what we would most likely order from apps to wine to desserts.
Little side note: The menu's on Disney's site are out of date. This site and Touring Plans are best IMO.
So for an 8 night stay, the Deluxe Dining plan gives 2 people a total of 48 dining credits and works out to be $1859.92 and we're using mostly signature restaurants with the other table credit for either breakfast or lunch. We're also doing 3 counter service and have it spaced out and worked out so it would fit our schedule in the parks.
Also there were some modifications. For one, if we were paying cash, we probably wouldn't order dessert alot because I don't normally eat it after a huge meal. Maybe a few meals. Also I did not take into consideration the refillable mug for two and all the snacks. I did not include those.
The breakdown for 2 people for 8 night stay:
Paying with cash: $1942.50 including tipping 20% at ALL table service restaurants
Deluxe Dining Plan COST for 8 nights: $1859.92 <- This is how much more you pay in the Disney World package price whether you get the Deluxe Dining Plan or not. For 8 nights that is.
Deluxe Dining Plan bill: $2137.50 including tipping 20% at ALL table service restaurants (This is the receipt or bill the waiter gives you while using your table credits to show you what you WOULD have spent including tip)
I mean it's not much savings but it's savings and when you add in the snacks and refillable mug drink, it's worth it by a mile.
Edit: Sigh, so I messed this up because I forgot to add the tips onto the DDP package cost ($1859.92). Tips add up to $336 additional which makes this post kinda moot. Sorry guys.