If the train used only regular type cars and moved below 40 km/h, I don't think there would be any problem. But with higher speeds and/or lower cars (e.g. some subway trains that also do "above the ground" strips), there would be a real risk of being moved around by the air pressure...
As for the last second issue, I think that was part of the bet: his buddies must know that lying between the tracks and waiting is safe enough, so they upped the ante.