There are couple of problems with letting the first person down set the landing direction. Unless the first person to land is well below everyone else jumpers that are already flying their landing pattern may not be able to safely change the landing direction they setup for. Also what if the first couple of people land at about the same time but in different directions.
If the winds are light and variable I think it is much safer to have the LO set a land direction before people board the plane. Just before jump run the LO should have the pilot radio the DZ and ask what the ground winds are doing. If the winds have changed the LO can set a new landing direction.
693:2 Both cutaways were about 5 years/400+ jumps ago.
The 1st was a cutaway from line twists when I pulled around 2200'. If I pulled by 2500' (which I do now) I could have cleared it. The 2nd was a CRW wrap at 11,000'.