Hello, Kris!
In looking over your earlier questions, it looks as if you were planning a trip this September, and the "extra $1,000" you mention above is due to a change of resort.
In order to best consider the value of the free dining offer, add up the cost of the food you would have ordered otherwise if
not using free dining. For example, would you have purchased a Dining Plan? Would you have paid out of pocket for your meals and grocery orders? Calculate that total and then compare it to the additional cost of having booked a more expensive resort in order to take advantage of free dining this fall. This will give you a better idea of how much, if anything, you'll have spent over what you would have spent at the other resort.
Regarding this resort, there are so many folks out there who love, love, love
Disney's Wilderness Lodge so much that they simply never stay anywhere else! Take a look at all of the information available on this link first, and then continue to read about the resort on the
unofficial Disney fan site, allears.net. There, search under Walt Disney World accommodations, and you'll find lots of photos, information and reviews of this beautiful resort. Remember that you can take a boat to Magic Kingdom Park from WL, as well.
I also suggest using allears.net in order to add up the cost of the meals you'll be enjoying on the Dining Plan, then compare that to what you've spent to upgrade to this resort. When we are on a Dining Plan, we order entirely differently than if we are paying out of pocket. So, while I may have paid $15 for a Cobb Salad at The Hollywood Brown Derby if I were paying cash, I'd absolutely order something far more substantial (and expensive) if I were on a Dining Plan.
Please send any additional questions as you think of them! We love to help!