My family is using TiW for the first time next trip. Its good for us because we stay off site so we don't have a choice of the DDP. Also, since my winter trip will be offsite and my spring trip will be onsite, it will keep saving us money!
Its not unusual for my family's dining bill to be close to $300 (there's 7 of us immediately..and we usually bring friends to the world with us so it adds up super quick!)
I actually spent a few hours one night pretending I was on the dining plan. I looked at the places I would eat at, and checked out the menus. If I paid out of pocket without the TiW card I would be spending less money than the DDP...so I figure going the TiW route would be a big money saver for me (especially since im fitting two trips on it!)