I am pretty sure that, in the late 1970s/early 1980s, (the late) Fritz Kott ran a T-roadster pickup..... I do not recall that it was a record contender but, it was a "stock bodied" classic style roadster which sat relatively tall.....
Personally, while NOT an aerodynamics expert, I am pretty much of the belief that frontal area is frontal area whether the car is wide and low or narrow and tall..... but a body panel that is set at an angle in the same frontal area will, in ALL likelihood, create less drag than a vertical "flat to the wind" panel....and the Cd is a consideration that needs to be factored in.
As a chassis builder, my big question would be - can we get you into or out of a seating position which you can enter/exit with ease as well as drive the car without your knees locking up etc (knee problems are MY problem - so - just saying)?