I feel for your buddy. I rode up with a couple guys once when I started out in the mountains and the driver refused to load my sled on his lifted F-350. Things worked out but I woulda loved having reverse back then!
A few years ago, watched a guy, parked parallel with the snow bank, hit his sled deck going probably 30 mph. Ski's landed on the roof, similar to this, then flopped off the side, ending up wedged between the door of the pickup and the snowbank....Not a very good day.
let my son (12) load his enticer 340 onto our trailer last year....too much gas, not enuff brakes....bent a ski and a hole in the offramp....I didn't give him crap, but he learned his lesson that day...oops....live and learn....seen those dented roofs PLENTY.
Then there's always the reverse scenario.....telescopic ramp and scratchers still down. Don't wanna say who the dim bulb was that did this....but I'm sure glad I was wearing my teckvest!