What direction are you hoping to go with the car? Street? Strip? Both?
The short shaft TH400 and the 200-4R are the same length, and you will only need to change the slip yoke. If it's a long tail shaft, then you will need to have the driveshaft shortened.
Reproduction W-Z manifolds are available, and would be a good way to keep it simple as well as keep underhood temps down. Headers give off a lot of heat into the engine compartment. If you go with headers, Hooker and Kooks are both good choices. Do Kooks wrap around the frame like the Hookers do? You'll need to make some sort of steering stop to keep the front tires from rubbing on the rear primary tube that wraps around the frame rail. Anyways, make sure to buy them painted,
not pre-coated. Fit them, pound as necessary,
then have them coated. Out of the dozens of sets of headers I've installed, I've never had a set that didn't hit somewhere and need to be modified(pounded on). Never. So plan on it if that's the route you take. You also may have to re-route some brake lines to keep them away from the heat. I haven't done this on my car yet but I plan on it, cause when it starts getting warm from heavy idling, the pedal starts to get soft as the brake fluid heats up.
Assuming your car has a/c like 99% of Cutlass' do, it will narrowly clear the heater box with stock height valve covers. If you have a non a/c car(like me), you will need to make a notch in the heater box to clear the back of the cylinder head. If you run tall valve covers(like me), you'll definately have to do some notching of either type of heater box. If you have no heater box at all, then you have nothing to worry about except getting cold.
Hope that answers some of your questions, let us know if you have more. There's a few of us on here with 455 Olds swapped in. And trust me when I say you're going to love the 455...