the 285's will fit with no problem at all... i have 315's under my truck and they fit just fine too... the dealer is right about the reflash to correct the speedo i think on the 285's. the 1500 series rams with the 20" wheels & 4x4 have 33" tires right from the factory [275/60/20's i had them on my red 1500] and the 285/70/17 is the same overall diameter as the lower profile 20"s... the dealer should be able to flash to that setting to correct the speedo. [the body computer that handles the dash display should have that size in it's memory]