Block out of square

Just remember that the trans input shaft is a snug fit into the crank pilot bushing. So once you stab the input shaft you're going to tighten the trans flange bolts which will raise the tail end of the trans about .050-.060" (if you don't have the back of the block square to the crank) and put undue stress on the end of the input shaft which will transfer into the input shaft bearing, etc, etc.... that would definitely not be a good thing???

No, agreed -- I do care a lot about getting the tranny so that it's in angular alignment with the crank. So that would mean either machining the taper out of the block, or machining a matching taper into the bell, or shimming the taper out, such that the angular misalignment is resolved. Any of the three of those solutions is, yes, going to mean that the bolt holes in the back of the block which the bell mounts to, are now no longer perpendicular by, as you said, 0.4 deg. The "does it matter" question was centered around the fact that it seems much more important to worry about resolving the the input shaft alignment than that the bolts remain 100 percent perpendicular.