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How is the block not going to like that any different than a comparable 440 built the same way? You can get wedge heads that flow the same as his stock conversion stage v heads, after that the rest of the build is a wash. If he's going for high hp and high rpm he may need stuff like aftermarket main caps/studs, block girdle, etc. But it's not like a 440 has never been taken that route before. IMO it depends on what his overall hp goals are.
Go that rout if you want, but I would not spend that kind of coin to put a 2-bolt RV block under it... 
Blown up enough hemis to know where to put the money.
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