Will a Chevy 350 motor and tranny bolt to Oldsmobile driveshaft?

No, a Chevy 350 motor and transmission will not directly bolt to an Oldsmobile driveshaft. The bolt patterns on the Chevy transmission's output flange and the Oldsmobile driveshaft yoke are different. You'll need an adapter to make them compatible. This usually involves a custom driveshaft or an adapter that changes the yoke to match.