I have. We have had two tongues break because of the buffeting from the tailwind of the motorhome, causing the trailer to start whipping from side to side. This has only happened with trailers that have long tongues that do not have triangulated supports from the front of the tongue back to the main frame.

Some people trailer their boats backward on the trailer, and one reason that some do it is because with the sharp bows facing forward, the bows catch the wind and can get an oscillation going.

Other people trailer the boat backward just because it is easier to raise the mast when it is sitting up on the trailer mast stand and you don't have to do that initial cling-and-jerk maneuver. (But if you drop it, you will probably dent the top of your vehicle.)