Do you start with a cat trailer and then throw the ply deck on? Or did you start with the utility trailer and use it to drag around the boats?

My father in law is in his 50 and has a bit of a bad back. I'm trying to get him on the water quicher and easier so he only has to step the mast, raise the sail and go! Any hints for easiest trailer setup? Flatbed and cattrax? do you trailer with the mast in one piece?

Dan