If you were closer we'd probably be talking, especially if your fronts are the -3AA revision which are (hopefully) less hassle with the center caps/hubs. I'm getting ready to buy a pair of new 8.5's although I already own a full freakin' set, but the ones I already have are the 4.75" backspace and also the old revision so they're fine on a stock height truck if you run a spacer up front, but worthless in the front for a dropped truck.
Kinda surprised to hear about the issue with the rears. I've already rolled the lip in the back just because I drive that truck like it's a Corvette, probably didn't need it with the current combo but I figured better safe than sorry. Does it really need to be cut with the 10" 338's or was it due to the tire size you picked?
Im gonna go with the 255/45 up front with a 295/40 out back.... Should look good.
I think that's what is already on the back of mine with the 8.5" Centerlines, when I sold the truck to a friend he mounted those up and I'm getting ready to swap on the 338's because the girlfriend likes them better and she's the one driving the truck now; will have to check them in a bit when she gets home. They look slightly taller to me than the 255/45/20 fronts.
Kinda thinking I would just round out the package with the 10's out back since I was already gonna have to buy new fronts, that way I'd have a whole set of old revision 8.5" / 4.75" bs to sell off instead of stuck with a pair I have no use for.
Richard