I would go with whichever one you think will survive more on the trail, maybe whichever one you can see better to make sure you keep if off the trees. I have mine mounted on the driver side to keep my antenna (102") out of the trees that overhang the side of the road. On driver's side also makes it easier for me to get out and tie it down. Not as much of an issue with shorter antennas though.
As far as signal... for "trail" use neither is better than the other. The signal will be skewed slightly to the opposite direction from where it is mounted. Passenger rear will be skewed towards the drivers front and vise verse. This is really helpful if you are driving down the road as your signal is skewed towards oncoming traffic rather than off the other side of the road.
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