To choose between them, you'll be miles and smiles ahead if you put something in that FITS with virtually no modifications, such as the 350. Looks the same dimensionally as the 260, yet is way better on performance.
As far as build, you can do anything your heart and wallet desires. Issue with BBO in the 78-88 Cutlass is that there's limited room under the hood to do anything crazy like tall intakes, spacers, etc. with a 455. Unless you start cutting hood holes or buying scooped hoods, just adding to the expense.
Can you do it? Sure. But you'll need to modify some A/C brackets if you want to keep your original pulley setup, etc., with a 455, or just swap them over to a 350, for example. Put a TH350 behind it, and you're set for a great fully streetable situation.