Due to the age of the motor my guess is that its already been bored to .060, and may have heavier that average wear. Unless the innards are pretty much pristine I'd rather spend the money now and go back to standard rebuild than wait for wear to take it past a rebuild-able state. Just my preference.
It also seems that 'metal shim' type head gaskets are an option instead of the thick metal/fiber stock type?
Again, not knowing any better it would seem that the thinner head gasket and taking a moderate cut off the head (say .020 to .030) would be a winner with no real downsides or a super high cost.
Is there a cross reference of 50's heads and the cc's online?
Of the two blocks I have, one block number is 3692713 and this is a babbit/dipper motor (If I did the lookup right) and not really an option (but it does run).
The second block number is 3764476 and this is the most likely candidate if not cracked. I have another motor but not sure of the numbers... most likely a late 50s.