FYI we were just there last week and had issues, too.
We had booked the Ultimate Christmas Package and also a dining package. While we've visited WDW twice beforehand, tt was our first for both packages. When we checked in, I asked the person about the Ultimate Christmas Package and if we needed anything for the events. He said, "nope, just use your magic bands." I then asked about the dining packages and for him to double check that we have them. Also asked information about how to use them. He just said "it will automatically happen at the counter service." Then hustled us out.
Fast forward to lunch, we told the counter service person at Hollywood Studios that we had had a dining plan, they just asked that we scan our magic bands and that was it. I thought it was strange though, since it showed a dollar amount instead of an "amount remaining" which is what I read it would show me. Later, we went to a table service dinner at Epcot, and the waiter basically said we didn't have the dining package. It wasn't showing up in our account. We spoke with the manager, and she tried calling the hotel, but CBR's back office did not pick up. The manager then tried calling Disney directly. I could barely hear the person, the person put me on hold, then hung up on me. In the mean time, the manager told us to sort it out with CBR later.
Later, someone from Disney called my wife while we were on the boat to Hollywood Studios, and it turns out that even though we had booked with Disney, Disney screwed up and didn't link our dining plan with our account because they had been booked separately. So, the front desk person at CBR screwed up by not making sure we had our dining plan linked, even though I repeatedly asked him to. In any case, Disney now said they needed a cc to complete the new reservation with the dining plan. I didn't want to give out my cc in the middle of a boat ride to Hollywood Studios. What they didn't tell us was that when they switched the reservation over, they removed all charging privileges from our magic band. Luckily, we had kept our gift cards with us instead of leaving them with our luggage. But, it was frustrating because that was our only day at Hollywood Studios.
Then, when we got to our exclusive event at Hollywood Studios, they wouldn't let us in unless we had some sort of credentials. Luckily, we managed to speak with the manager of the event and he gave us the credentials. It turns out, CBR was supposed to give us the Ultimate Christmas Package envelopes when we checked in. They were delivered to CBR on Friday and we checked in on Monday. Again, the front desk person screwed up because he didn't give us the package even though I repeatedly asked him for it. The manager of the event indicated that CBR had other issues with this package, too, and that we weren't the only ones.
When we spoke with CBR, the manager's first response after hearing my frustrations was, "Oh, I can refund you your stay and you can leave if you want." That only compounded my frustration (yeah it was close to 11 p.m. at night - where are we going to stay the night and how are we going to book a last minute flight home). He eventually came around and redeemed himself by providing some credits for us and also providing 3 fast passes x day. He also sent a snack and water package to our room the next day.
I will say we did have one other snag that I didn't bother raising - I had asked about our Magical Express confirmation for our trip back to the airport for our departure, and they said it would arrive the night beforehand. It never came. We had to go to the bell service to get a printout the night beforehand to serve as our ticket.
Summary:
1.) Disney screwed up by not linking our dining plan, even though we booked through Disney (so they can't even blame a
travel agent).
2.) CBR front desk screwed up by not checking that our dining plan was linked when requested to do so.
3.) CBR front desk screwed up by not checking that our Ultimate Christmas Package information was delivered to us, even when specifically requested to do so.
4.) CBR manager screwed up with his initial response to basically refund our stay so that we could leave (we had flown in as part of a package).
5.) CBR manager did redeem himself by providing compensation, and 3 x fast passes per day. He also sent a snack and water package to our room the next day.
6.) Disney also didn't provide us with our Magical Express confirmation for our trip back to the airport. It was never delivered to our room as they said it would, and we had to specifically get it from bell services.