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It all comes back to, how enthusiastic about the project are you?
If you are living on welfare, go as close to stock as you can.
If you are reasonably comfortable, go 3/8 x 3/8. It is not all that expensive for a big STREET engine and DO NOT let anyone tell you the cubic inches don't matter in a flathead.
Once you step on the throttle of a 296 you will be hooked forever.