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best choice would be either the 2001 bmw 740il or the caddy. the drivers car is the bmw while the caddy is the more tech/feature filled car. jaguar is the fastest, but being supercharged that's one more moving part to worry about having issues with on a 13 year old car and that engine is prone to head gasket failure which would cost between 2500 - 4500 to fix. 750il: had a lot of recent work done, has more miles than the 740, and do you really need a 12 cylinder. mercedes is the oddball in your options. its a 2 door "sporty" coupe vs every other option being a 4 door touring car + the mileage is crazy on it. i'd personally go for the 740 vs the caddy because i actually like to drive my cars, but if you prefer all the luxury options and don't mind something that drives like a boat the caddy wouldn't be a bad choice either.