#1: My daily driver would be a 2012 FIAT 500 Abarth convertible. White with red stripes.
#2: My cruiser would be a 1957 Ford Ranch Wagon. Can it be modified? If so, I'd go with a modern Mustang drivetrain (the new 5.0 Coyote motor, 5-speed trans, new Mustang rear end). Airbags on every corner. Not sure on color yet, but either black or red.
#3: My streetable race car would be a Bradley GT kit car on a full tube chassis, with a Toyota Matrix drivetrain (in back). I'd like to keep the old-school huge metalflake gelcoat intact, preferrably blue or purple, but red would do.
#4: My hauler would be a modern F250 diesel quad cab with a 5th wheel. And it has to be gunmetal grey. Can I get a trailer with it? An enclosed trailer capable of hauling 2 cars and a full pit setup?
#5: My off-roader would be mid-80's Jeep Grand Wagoneer. Lifted, big mud tires, upgraded axles, roll cage- the whole 9 yards. Whatever color it is doesn't really matter, you won't see it anyway.