Okay, bear with me. I know it makes better fiscal sense to start with a larger engine, but certain racing classes would require the stock head, block and intake manifold castings for a '55 or '56 race car. Just how big could you make the '55-'56 Chevy V8? I'm thinking that if one were to take a 265 out to the max overbore (someone said 283-size) and then offset grind a 350 crank based on the smaller journal size you could net a rather large engine for your F.A.S.T. '56 150 sedan on the blackwall bias plies and dog dished steelies.
you're right about the waste of time and money, but if you have both. Dyno Don Nicolson built a blown 450+ cu.in. 283 back in 58-59 that was by far the biggest that I've ever heard of and it was in a 4 door model A. claimed that he bored in to the water jackets and sleeved it. then ground the block to clear a 5/8 stroker crank built by Hank the Crank. never heard it run but I saw it at his house when he was still running the Dyno at C.S. Meade in Pasadena