You've got a good opening, but you try to cram too much stuff into a single sentence (a fault I recognize because I too often do the same)."Ockley dropped pages to the deck and rolled his eyes at his driver."
If the driver's name is Webb, use his name the first time he is introduced. Also, I got confused trying to picture the relative position of the two characters. Third, you roll your eyes at someone looking at you, drivers usually have their eyes on the road. You probably need at least three sentences in place of this one.
"Webb squatted at the edge of the turret, somewhat elevated over Ockley's recline on the residual engine-warmth of the back deck.
Similar problem here. Is Webb the same person as "the driver"? "Turret" suggests that the "driver" is driving a tank. If so, why not say so. But tank drivers drive from inside the tank, don't they? Ockley isn't really reclining on engine-warmth, he is reclining on the back deck (which now suggests boat or maybe, together with turret, submarine) feeling the engine-warmth (which is a nice tactile image).
“Webb, I can't read this. T'is personal.”
Who is speaking? Ockley -- but the first sentence gives the impression that he did the writing. A third party?
“So?” Webb said without pause to his furious writing on the much-abused pad he held on his knee. “We're four guys living in like ten feet square and we kill for a living. I think we got personal covered. 'Sides, I start all my letters that way.”
Now, having read opening three times, I'm beginning to get the idea that the pages Ockley drops are not pages he has written, but that certainly wasn't clear on the first two reads.
“Chief says 'Hi?'” Ockley grumbled, grudgingly raising the pages back to his squint, “When the hell have I ever said 'Hi' to anyone?”
“It's a funny image I think,” Webb admitted.
And the dialog here is fine. All you need to do is set it up. Something like, "Webb, Ockley, Scotty, and Sulu were riding across India on the back of an elephant. Webb handed Ockley the letter he was writing."
Then you can go into the dialog, which is good, without loosing the reader.
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