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There are actual 'standing operating procedures' for 'tactical road crossing' out there, but the long story short is: Someone exposes himself for a while and may get shot along a straight road. The fewer expose themselves at the same time, the more may be hit by a machine gun burst, but the less may be hit by a sniper. The fewer expose themselves at the same time, the longer the road crossing takes and the more likely some hostile can ready himself for opening fire. There will always be risks, and persistent risks will mercilessly decimate the force over time.
In the end it's the same as with river crossing; best done on the top of a U-turn, but then you have troublesome terrain on the other side.