Bought TIW during my December trip.....using it in June.
The mandatory gratuity made me feel sort of cheated. Mind you, I always leave at least 15%; my wife worked as a waitress in the summers during school and I always leave a tip. Based on that tendency to leave that kind of tip, it still works out as a great savings.
Deb, Bil and others suggested exactly what I would suggest. Plunk down what the dining plan costs on a gift card. Even paying for the TIW 100.00 card up front, the TIW almost paid for itself in a three day trip. That makes our June trip, well.....gravy
We have had to adjust our eating patterns based on the age of our kids (8 &11) and our own preferences. Our plan for eating now is breakfast in the room or a QS visit (30.00). We either eat a snack type lunch (a kids meal for the kids at QS and one adult entree-two meals for 4 folks and then an ice cream or popcorn) that's about 30.00. Then dinner somewhere. Normally, we hit two big ticket restaurants(two dining credits) during the trip. Last meal at California Grill was $175.00 minus dining plan allotment I still paid about 95.00 with gratuity, wine and extra desserts. With TIW it would have been cheaper, based on the double dining credit and stuff not included on plan.
Magic bands also are an advantage from a cost saving standpoint. Same as KTTW. We use our bands to pay for everything. I get a printout from the CM at the resort desk in the evening and that way I have a list of what we have spent...easier than trying to add up 15 receipts. That way I can track spending against what I put on the gift card my "Dining plan." It is an easy barometer for seeing what the savings is. My experience is that TIW and gift card is equal to or better than dining plan AND you don't lose the money if you don't use the credit. It just pays for your "Glow with the Show" ears instead.
My 2 cents.