That's easy. If the engine has enough block and component strength, and has an experienced and competent builder, with a tuner who understands how to tune for volumetric efficiency, then the motor should live without issue. In other words , both should be reliable as long as those conditions are met.
You can't just say that one motor is always better than another because it is bigger. I see 363ci motors easily outrun 440ci motors plenty, and last longer.