Would it be possible to get a 440 to drop about 3/4 to a full point worth of compression by using the thicker head gaskets and the head gasket shims MP sells?
I am not sure if using head gaskets and shims in combination are really recommended anymore. I spoke with Hughes Engines last year and thye were to keen on it. I think the best bet is to buy Cometic gaskets in a thicker size. I know they will go at least to 0.074" on big blocks.
Put your values into a compression calculator and it will give you a good idea of what the difference will be.
http://www.rbracing-rsr.com/compstaticcalc.html