68 Cuda 383 vs a 360

When considering a big block, weight is something to consider. Although aluminum heads and intake and headers vs log manifolds will save a lot of weight. I also think the 'wow' factor of a big block is something to consider. I like the looks of a big block in an A Body. So what do you want? If looks and wow factor are important, a big block with dual 4s would kick butt. If you are willing to put up with a little extra weight on the front end, and are ready to absorb a few extra expenses for things needed for the big block swap, then go with the 383. Once the swap is done, you can fiddle with the 383 and get big power and torque from it. If ease of maintenance (383 is bigger, so less room left in engine bay) and streetability (slightly nose heavy A Body) Re important, then the small block may be your choice. Desired power is almost a moot point considering the amount of power you can get from a stroked small block. I would put a big block in mine, if I hadn't already spent so much money on the setup I have now.
Unless you have a specific goal that only a small block or big block can satisfy, I would lean towards the big block.