My boat was trailered backward (transoms first) when I got it and I have always done the same.

One advantage I notice is that, especially with my Nacra 5.5, the trailer can be a lot shorter and thus, the boat can be closer to the towing vehicle which makes it easier to back and park or turn around in tight places.

Also, with the boat trailered backward, the mast is already positioned above the boat and with a simple slide up the mast holder, the mast is stepped and raised in no time flat. Droping the stick is easy too becasue it just plops back in the holder and slides into trailering position. Shrouds always stay on and coil on the trampoline easily.

I am sold on backward cat trailering at least for this boat. See attached picture.