I tried a PRC1099 (5/20 multimode green radio) on 20M using a pack frame
16ft trailing wire and at-271 whip (10ft) and it was fun but the back didn't like
the all up weight of 40 pounds (radio was 33, plus water, and frame).
The whip was enough to torque the frame and pull the back, the
wire when moving can and did catch.
So lighter radio and stationary portable was the alternate approach.
Hazards, contacting low wires in some areas, tree limbs or other
low height hazards, terrain unfavorable to distance like valleys
and carried weight. An example is around me are a few old
bridges with 12'6" clearance, consider that with a 8 to 10ft whip
mounted. Rough terrain can be harder with added weight and
slippery footing.
Don't bend over as you may wack someone with the whip.
Allison