You'll be there during HalloweenTime, one of my favorite "seasons" at DLR. Last year, they added decorations to DCA (Buena Vista Street and Carsland), which really made HalloweenTime seem to be resort wide. They have not yet announced the dates for Mickey's Halloween Party (MHP), but might (should) also be happening while you are there. The dates (and details - there are rumors that it might move over to DCA this year) are usually announced in mid-summer (mid-July). If you can, I would try to go to at least one MHP while you're there. In terms of crowds, my guess is that the evenings will be busy, but the mornings might not be bad on the weekdays. The weekends are always busy during HalloweenTime. The first weekend in October (10/5-10/7) is when Gay Days, one of the largest unofficial events at DLR, is slated to happen along with Columbus Day (some folks get a three-day weekend). So, expect pretty big crowds on those days.
In terms of dining...my family's favorite TS places include Cafe Orleans, Carnation Cafe, RBT, and Ralph Brennan's Jazz Kitchen. For CS locations, we really like French Market, Plaza Inn, Red Rose Tavern, and Jolly Holiday.