Oliver 88 big bore?

It depends on how much work you want to do and how much you want to spend. Bores as big as 4.5" (380 cubes) can be used with serious block machining and using hard block. A more modest bore of 4.25" (340 cubes) to 4.375" (360 cubes) is a lot more manageable and if properly done allow coolant to be run. You should be able to run a 4" bore (302 cubes) without machining the block and using aftermarket sleeves.

Pistons are available from the usual automotive aftermarket suppliers that make custom pistons. A lot will depend on what you are going to use for connecting rods. There is nothing inherently weak with the original rods. Just do a search on the Oliver board for proper reconditioning as there were a couple of factory glitches that may need to be addressed.
 
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