I think this question all comes down to how thin you think the cylinders can be and still be reliable. After the block summit it became clear that going to 4.440 bore size really should happen after a careful sonic check. The only areas that will be potential trouble spots are about 1 inch down in the bore where two cylinders come together. It's normally a small area that is thin too. And generally it gets thicker before you're half way down in the bore. Generally the thrust sides are quite thick on these blocks and should not be a problem.
In the block summit info Wes' block is in there somewhere. It's a D1VE running as a 557 making around 900 horsepower. It's filled to the bottom of the water pump holes and it's been living just fine. It has a few cylinders with .085 or so in the thin areas.
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