Well,
As I work the problem in my head, It seems that using Tech's advice (a general practice) of mocking up the crank with pistons in the #'s 1,7,2, & 8 bores, measuring piston to deck clearance at each of these four corners, and then milling the deck to acheive the desired quench height with the gasket thickness to be used, ends up squaring and paralleling the decks to the crank centerline regardless of the required amount of material actually milled off the nominal deck height.
If I choose to run an .028" thick head gasket with a piston TDC height of 9.008" from the crank centerline, then I will need a Piston to deck height clearance of .0012 to acheive a .040 quench distance. This means that if the nominal deck height is at least 9.025 at the low end of each deck, that a minimum of .005" will get milled off the deck, increasing the amount of material removed at the high end of the deck. In this case, regardless of how much material is removed at the high end, I will end up with a finished and parallel deck height of 9.020". If the nominal unmilled deck height turns out to be lower than 9.020" at the low end then I will have to run a thicker gasket after milling and adjust my deck cut and head gasket thickness as necessary to maintain the desired quench distance - up to a zero piston to deck height clearance and an .040" thick head gasket.
Or, simply zero clearance mill the deck to the piston TDC height at all four corners to begin with and run a head gasket thickness equal to the desired quench height, but here's something to ponder;
Would it not be better to let the cylinder walls take as much of the quench pressure as possible, thereby reducing the potential for blowing an otherwise thicker head gasket? Are not thinner head gaskets less prone to blowing out? What about keeping he gap between head and cylinders as small as possible to reduce the amount of carbon build up?