We LOVE HDD, Hubby and I try and go at least twice a year (once for the regular show and once for the Holiday show...not much difference, just song changes and atmosphere). The food is really good, all you can eat chicken, ribs, corn on the cob, beans and Strawberry shortcake. You also get unlimited soda, teas, coffee, Sangria and beer. The show itself is fun, it is a western style Vaudeville show. Basically it is a song and dance group that has come to your town to put on their show. They are very funny and the the tunes are very catchy. They also incorporate the audience into a lot of it so it is more like an experience than a typical dinner show.
As for the dining plan, you would just need to tell them when you book that you are on the dining plan package and they will book it that way. They will probably ask for a CC number to guarantee the reservation (as they did prior to the new policy) but they will not charge it, it would just be in case something comes up and you cancel the package. You get the actual tickets for the show when you arrive, so you can pick them up at any Disney hotel Guest Relations (7 day to 2 hours before show time) or you can get them right at the show when you arrive (it is easier to get them in advance). At the time you pick the tickets up, that is when the actual dining plan will be debited for the show.