In 2003 WDW offered stay for 7 nights pay for 4.(I think End of Aug - Mid Oct.)
In 2004 WDW offered stay for 7 nights pay for 5.( early fall again)
Then 2005 Free dining came out.( early fall)
WDW must have thought it was a better promotion ( either more guests taking advantage of it or less costly to them ) because they offered it again in 2006,2007, & 2008.
It's a "better promotion" because it generated more of a response. And THAT was because it's a better deal. Let's face it, 4 adults willing to stay in a Value, splitting the cost of that room 4 ways, are paying about 25 bucks a head to be staying on-property AND eating. About 45 bucks a head a day for the same deal in a moderate. Taken on its face, it's a great deal. So naturally, WDW has since tinkered with the deal to make it less great while still seeming AS great (or, great enough) for the people using it. So, now the rooms where the deal is available becomes more limited. No big deal, IF you're lucky enough to get a room. Then they severely limit what children can order on the kids' menu. Then they start cutting into the variety of meals offered, because if every restaurant is only making 8-10 entrees (and if EVERY restaurant offers the same 3 or 4 kids' entrees), they save money by buying bigger quantities of fewer ingredients. Again, if you're eating for free, what do you care? But then it starts to affect the other guests who are paying for food of a lesser quality (and less variety) then what they used to get.
And to be fair, this is all also an inevitable byproduct of Disney's Magical Express. Now that WDW has the ability to make it
easier for guests to never go off-site, the incentive to make them
happy to stay on-site is less pronounced.
Now, what people are starting to see is the inevitable blowback. Food seems less appetizing, the Dining Plan (for those paying for it) is less of a value, and WDW keeps looking for ways to minimize loss during the free dining plan promotion, at the expense of the rest of the year. AND, as the OP confirms, lots of people aren't even able to take advantage of the free dining plan, and WDW is trying to offer incentives to keep those people happy (and not go off site) At some point, they're going to rethink the value/risk of the promotion, and probably decide it's not worth it. It's alienating the paying customers, and many of the customers taking advantage of the promotion find it not worth the hassle and (if they're not getting what they were promised) kind of a shell game.
Here's another potential solution, were they to keep the promotion going. It doesn't address the quality of offerings, but could conceivably make it easier for people to get ADRs. If you're on the free dining meal ticket, then for every 3 nights you stay onsite, you get your 3 snacks, 3 counter service meals and 3 table-service meals. BUT 2 of those 3 table-service meals have to be used during breakfast and lunch. And it keeps going like that for every additional 3 nights of stay, with the dinner table-service credit available after each 3rd night:
7 night stay? 5 breakfast/lunch options, 2 dinner options
8 night stay? 6 breakfast/lunch options, 2 dinner options
9 night stay? 6 breakfast/lunch options, 3 dinner options
Of course, this doesn't mean you have to wait until your 3rd night stay to USE a dinner option, only that your stay has to be at least 3 nights to GET one, and at least 6 nights to get TWO, 9 nights to get three, etc. This will force people getting the free meals to break up their schedules, not strictly use them for dinner (thereby also freeing up the space for more paying customers), and use them at breakfast & lunch (especially lunch, where portions tend to be smaller, and the cost WDW incurs to feed people for free will be less). I'm sure some of the people who are used to the dining promotion the way it is will be cranky-pantses about it, but IMHO, there are going to be more and more restrictions on the promotion anyway, this is the least offensive, the most fair to everyone on the plan, and potentially frees up some ADRs at night for paying customers, except of course at the restaurants that are always a pain to get adr's for.
