Keep in mind the so-called "
free dining" is just a promotional discount plan to keep WDW room occupancy high at times when the demand for rooms is low.
If Disney thinks rooms will go empty in October 2010, they're likely to offer "free dining," or "buy 4 get 3 free," or merchandise gift cards, or possibly something new to attract business. In any case, it's better business for Disney than selling rooms at actual discounted rates.
In a way it doesn't matter what the discount plan is. You're not paying as much as guests pay during peak-demand periods.
So the real question is what the demand will be in October 2010. School is in session in most U.S. school districts, but October has become a popular time to visit anyway. The Epcot Food & Wine Festival attracts adults without children, while Mickey's Not-So-Scary Halloween Party events attract families with young children who are not yet in school or who are in early grades when an absence of a few days is easier to handle.
In an odd way, Disney's resorts may actually be helped when Harry Potter opens at Universal's IoA. It will be compelling reason for more people to come to Orlando.
In the end, it will probably depend largely on how the economic recovery goes more than anything else.