Aerodynamics has A LOT to do with modern tractor-trailer tractor design. When you are on the road every day, improving from 7.0 mpg to 7.1 mpg via aerodynamics is HUGE. The trailers are standardized - and many modern tractor units are designed to optimize airflow of the combined tractor and standardized trailer in the interest of reducing drag.
Note how the roofline blends smoothly with the roofline of the standardized trailer, and the side fairings extend back as far as possible to minimize the gap between the tractor and the trailer, and the fuel tanks are faired in to keep the airflow out so that it does not go headlong into the face of the drive wheels.
For the original poster, the frontal area of the trailer will absolutely affect the fuel consumption of the vehicle. If the trailer is more-or-less within the frontal area of the truck, it won't be too bad, but extending out from the frontal area of the truck means the trailer will be outside the wake of the truck. The drag will be more or less in proportion to the frontal area (width x height).