Into the wind isn't a huge problem. Worst for fuel mileage is a three-quarters wind. Constant steering corrections.
That, and in areas of gusts across the rig (versus fore & aft) are the test for remains lane centered. Both vehicles.
Worst scenario is a narrow lanes road with oncoming big trucks too close together (illegal to do so, for this reason) as the air reverses speed instantly, and at the speed they are traveling plus your own speed. Loss of control accident is imminent.
Same for descending grades when passed too close by big truck. No tension on hitch, and it's enough to upset things. Or, why diesel engine exhaust brakes ain't so great. The TT brakes need also be applied (no matter the engine type in the TV) on grade descents.
1990 35' Silver Streak Sterling
; 9k GVWR.
2004 DODGE Cummins 305/555; 6-manual; 9k GVWR.
Hensley Arrow. 10-cpm solo, 18-cpm towing
Sold: Silver Streak Model 3411