It's been a while since I built a V-8, for the last 10 years or so I have been playing mostly with 914 4 cyl Porsche motors. I run Piston & cyl's sizes anywheres from 4.130" to 4.180". But the issue with these are cyl to head sealing, chamber sizes, valve shrouding, all critical areas during assembly. Fixes, using lapping compound to lap cast iron cyl's to aluminum heads to help them seal, copper head gaskets, and other assorted fixes. Chambers that have to be small enough so the cyl's have surface area large enough to seal against, which in turns shrouds valves and the fix for that is high lift, which gets the valve out of the chamber that's shrouding it.
So, recently I was looking for gaskets for my 390 build, and remembered that the last time I used factory steel shim gaskets, so was looking for a set and the ones I found the bore dia was 4.410". My bore size is 4.090, so that would leave .160" from the bore to the gasket, which is a lot of wasted area that could be used to seal the heads. I 've found other gaskets that have a bore size of 4.180", so .045" from the bore to the gasket is much better.
And for my 427 build, I did find Cometic makes MLS 4.250" bore gaskets which match my bore size.
Who knows, maybe I am getting anal in my old age...
... Or how about it's the devil in the detail gained from experience...
...I like that explanation better.