It will depend on your trailer and the position of the trailers axel as to how the weight balances. with a 16 you will leave the rudders on. You just have to make sure the trailer tounge is long enough so that when your tow vehicle is at 90 degrees to the trailer that you don't smack the rudders with the car. I use a trailex trailer for a Hobie 16 with a Dart 18 and trailer the boat backwards. (properly from my perspective) The mast raising is straitforward just as you note. Push the mast forward in the front mast caddy. Pin the mast. hop on the tramp, raise the mast, have some one pin your bridle and forstay.

The down side is that if the mast ever drops out of the caddy as you push it forward ... you dent your car's trunk... big problems if you every drop the mast when you are lowering it.