With a trade located in IL he will be hard pressed to not loose money on shipment even if ST offers him what he owes on it sight unseen...plus, with IL lease tax laws a lease deal will not be attractive regardless of purchase price. The minimum courtesy delivery fee of $500, possibly more depending on dealership, will eat away at any savings he can get from not using a local dealer.
While I agree ST can get him a great deal I believe all the peripheral factors associated with the OPs location will overcome the ST discount.
Current Car: '13 SANTORINI BLUE E92///M3
--6MT/Speed Cloth/ZCP (ED Thread)
Former Cars:'10 E90 335i MSport
/ '07 Interlagos ///M5
/ '09 135i
/ '10 E93 335i