Last year Microsoft boosted Holiday sales with $50 off promotion that started November 2nd. Seem like Microsoft is in a good position to offer the same deal this Holiday season with so many of its bundles price at $399-499. They would not even be taking a financial lost on these bundles.
I would think if Microsoft will have the $50 off promotion it would happen before Halo 5's October 27th release. Microsoft can't afford to lose this Holiday and I think this price cut is all but certain.