Not Jay but....
It would be helpful to mock-up the block with the crank, pistons and rods (say 4 corners) and with the selected head gasket check the quench distance. Hard to do now of course. Yet, if it's a streeter and not a race engine, I'd say save the $ on the 2nd pass. Still, if for example the pistons still end up in the hole with an assumed .047 quench distance, with .040 or so being ideal, then yes, a 2nd cut would be helpful. I guess it depends on money, as always, and time.