As a utility contractor I can offer a few tid-bits on this matter.
Volume, pressures and depth are no where near the same now as they were then. As tech progressed we got better at all three. When you go surveying for for oil (or natural gas like I have experience with) they tend to progress together fairly evenly. Since that site is about two miles under water that puts the other two categories proportionately high as well.
Also worth noting they have a 22 inch drill casing bellowing “peanut-butter textured” oil (or so I have read in trade magazines recently) into the gulf. Up until the 70’ I think 2-1/2 or 3 inch casings were the standard. Even if the casing was bigger say for example a five inch casing is was still reduces to 3 inches to go through the pump systems. All fire engines still do this today.
(Not that this has come up so far but…) I’m not sure when off-shore drilling became popular but even then we didn’t need to because of the number of land based oil sites at the time. So this factor can totally be eliminated from this equation.
As far as transporting goes a U-haul size box truck was the standard method of travel on land then not the 53 foot tractor-trailers we commonly see today. Your container ships have evolved in much the same way. So each loss would be marginally smaller. To put things into perspective the Exxon-Valdez oil spill in Alaska was estimated at 10.8 million gallons.
Lastly I think it should be worth noting that the demand for oil although great wasn’t like it is today. Most US tanks at the time ranged 3-4 gallons per mile (not miles per gallon) and ran off of a 8 cylinder gasoline engine. When the US entered WWII we only had 15 modern tanks.
So every thing was at a much smaller scale then as far as harvesting and consuming oil goes.