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With most windsor blocks, 30 over bore is the most recommended due to possible pinholes in the casting. A machine shop should be able to magnaflux the block to see if you can safely go more. Have seen a lot of blocks bored 40 over with no problems.
I run a '81 351W block in my drag truck. It's .060 over and I spray 200 hp of n2o on every pass. If it's got one 1/4 mile pass on it it's got 1000. No exaggeration here. After the first 1200 passes, I took the top off one of the Badger cast pistons. Sleeved it and put in a set of Keith Black hypereutectics and it'll still pick the front tires off the ground and run 10.30's all day. It's in an '87 Ranger BTW.
Will the roughly 4 cu. in. gained in displacement from going .030 over to .060 over really be worth the possible loss of reliability? To be safe I wouldn’t go past .030