I haven't read through this entire thread. Here's what we've done for DDP:
trip 1- 9/2003- Stayed off site...no DDP and ate off-site
trip 2- 3/2005- POR and DDP (was @ $37/day and included apps and covered tips...great deal...and our kids were 6,6, and 8...so they were like $10/day)
trip 3- 9/2006- BWV and DDP- 1st time using our DVC points...took my mom...still liked the DDP (kids were still kid prices)
trip 4- 1/2007- couple nights at the Contemp (DH had seminar there for work)-no DDP, paid OOP...then 3 nights at SSR with DDP...MIL and FIL were also at SSR (for a week with the DDP). DS turned 10 a couple days after this trip, so we squeezed out one last trip paying kid prices for him. Still like the DDP. We did the Concourse Steakhouse, HDDR, the Luau, LTT and Olivias.
trip 5- 7/2008- 4 nights at BWV and then 5 nights at VWL...with SIL and her family of 5...all on DDP...DS was now adult prices and at this point tips and apps weren't included anymore and the cost was in the 40s. We still liked DDP somewhat, but were beginning to become disenchanted. We had deluxe DDP for the 5 nights at VWL and realized that was too much food...too much time spent eating...too much $$$ and we'd never do it again.
trip 6- 7/2009- 5 nights at HHI and then 3 nights at OKW (no WDW parks this trip, so no DDP) we spent 1 day at SeaWorld and 1 day at Downtown Disney. We ate at Cape May, Ohana and T-Rex and paid OOP.
trip 7- 7/2011- week off-site...for DDs softball World Series...got annual passes since we'd be going back in Dec. Spent 2 days in the parks and went another day for a quick visit and to eat at Biergarten...paid OOP.
Next trip #8- Dec...6 nights at OKW with DH's entire family...no DDP, but will get TIW card. Have TS dinner or lunch booked for every day (LTT, HDDR, Bongos, Ohana, Biergarten and Rose and Crown). Have 1 breakfast at Olivias booked also.
Since we stay in DVC villas, we get in groceries for breakfast and do 1 CS and 1 TS per day for lunch and dinner. We found that TS lunches work better for us and are cheaper when paying OOP. When we really began to give the DDP some thought, back in 2008, we did some calculations and realized that we'd have to do all-you-can eat or character meals or choose the most expensive entres to break even on the DDP. Maybe we could even save a few bucks, but we wouldn't save a significant amount. And we didn't always want to order the most expensive entre or always get a dessert and we like to get adult beverages and/or water with our TS meals. Sometimes we just like to order apps and no entres. My inlaws don't like DDP anymore either because they like apps and entres but no desserts or snacks.