are there any modifications done to the 455? does it have a 4bbl carb, or 2bbl?
... I know this is not what you were hoping to hear, but I don't even think it's a competition. Even stock with emissions and a 2bbl carb, that 455 is churning more bottom end torque than your 305 can make with heavy modifications. And if it's got a 4bbl carb, it's looking grim for your Cutlass. And don't think you have weight savings on your side... that 455 is the same weight as your 305.
You're not helping the 305 with that big 750 Holley carb. You're going to give up alot of throttle response, too big a vacuum drop when you hit the throttle, not enough velocity, not gonna make any torque. And you won't see the horsepower gains you want up top because those heads are out of puff around 4800rpm. A well tuned Qjet carb is more sensible
If you're changing gears, your car will feel quicker with 3.73s or 4.11s. But that depends on the gas mileage you're willing to live with considering if you have a 3spd or OD transmission. Shorter tires can also add effects of bigger gearing.
A cam would be nice, may add some top end if it's not to radical. Run 50/50 mix of 114 high octane fuel and advance the timing a touch, you'll pick up some torque. And find a way to run forced air with a open airfilter.
Your dad's regal has suspension advantage too. If it's a T-Type, likely to have f41 suspension with rear sway bar. He'll see better traction off the line and put that brute torque to good use.
... sorry man, I'm putting my money on your dad's Regal