Okay, I'm just back from a quick weekend to the world. DH and I did NOT use the DDP, as we worked out what we'd most likely eat and realized while we'd only save $7 on the DDP, if we paid out of pocket and used our DDE card, we'd save over $45 - that made the choice a no-brainer. I understand that not everyone loves to plan and will sit down with menus months in advance to decide what they'd like to eat, which makes the DDP and the minimal savings attractive.
But I had to report on our experience with the plan this past Sunday night, 2/10. We met up with friends for dinner at Chefs de France. They had the plan, and they also ordered two glasses of wine and an appetizer - neither which are included on the DDP. When our receipts came out, there's was VERY messed up. The waitress applied their DDE discount to the wine and appetizer, but then wound up adding the automatic gratuity to the ENTIRE bill (including DDP items). What she was supposed to bring were two separate checks - one for the DDP and one for any additional items, but instead everything was grouped onto one check. The 20% discount was applied to the WHOLE bill, and then the 18% tip was added to the WHOLE bill. It took 25 minutes for the waitress to sort this out, and in the end, she still didn't remove the total gratuity - she only suceeded in splitting up the bills. So all the theory of the 'convenience' of the plan did not apply in this case. Not only did our friends have to carry around extra money and other cards to pay for their dinner in addition to the KTTW card, but we all had to sit and wait for the restaurant to figure out how it should be billed.
I want to point out that this had no effect whatsoever on our dining experience - the food was great and the service was excellent - it's just another little annoyance of the new DDP.