Flying airplanes in extended formations, with separation distances of tens of wingspans, significantly improves safety while maintaining most of the fuel savings achieved in close formations. The present study investigates the impact of roll trim and compressibility at fixed lift coefficient on the benefits of extended formation flight. An Euler solver with adjoint-based mesh refinement combined with a wake propagation model is used to analyze a two-body echelon formation at a separation distance of 30 spans. Two geometries are examined: a simple wing and a wing-body geometry. Energy savings, quantified by both formation drag fraction and span efficiency factor, are investigated at subsonic and transonic speeds for a matrix of vortex locations. The results show that at fixed lift and trimmed for roll, the optimal location of vortex impingement is about 10% inboard of the trailing airplane's wing-tip. Interestingly, early results show the variation in drag fraction reduction is small in the neighborhood of the optimal position. Over 90% of energy benefits can be obtained with a 5% variation in transverse and 10% variation in crossflow directions. Early results suggest control surface deflections required to achieve trim reduce the benefits of formation flight by 3-5% at subsonic speeds. The final paper will include transonic effects and trim on extended formation flight drag benefits.