For me it's a toss up between Classic and Caravan; get a canteen and possibly the only 10mm pistol in all of the Majove Desert, or binoculars and a shotgun that is to my tastes. In the end I'll probably go with Classic because I always pre-order with Gamestop; but really, what does it matter? For those of us who plan on getting the PC version we'll get one through pre-order and the rest through mods;
I doubt there will be just one 10mm pistol in the whole Mojave Wasteland. They're not going to give you a gun but not give you any bullets for it.
I can garuntee you that once the game is released one of the first mods will be getting all the pre-order gear in one neat little package.
Maybe. That might run into legal issues though.