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The old man at my local machine shop said it well when I asked the same question. He said "I'll bore it, but if it breaks in half you get to keep both halves".
I think it really depends on which block you have. Some of them have more material than others. It has something to do with the webbing at the back and inside.
I'm not gonna go with that high $$ 445 stroker kit, I'm just gonna go about .030" over and use a 428 crank. The kid inside me wants a really wild engine for my old '69 F100 but my wallet keeps saying it will still burn the rubber off the tires without alumium heads and a dual quad carb setup.