I prefer to trailer my boat wide.
My steel trailer is very tight, I welded a 1/2" nuts to the outside tubing of the telescopic tubing and tighten a 1/2" bolt at each "arm" so the is no flex at all in that telescopic mechanics.With my boat left wide is has remained rigid all these years. When I trailer the boat retracted ( only the first year I owned it '89), the boat seemed "loose" on the trailer which I didn't like.
My setup up time is about 45 minutes with help from my crew. With the boat disassemble, the setup time is over two hours. Remember, you will need to tighten your tramp each time you extend the boats frame. And you will need to store that tramp off the boat so the wind from trailering doesn't damage it. A tight tramp is a tight boat...
I solo sail my boat at least half the time. I can get nearly all set up and just ask for help with my winch to raise the mast. I build a crane style forward mast caddie that works well. If I use a 10' ladder to elevate the mast behind my rig the mast goes up much easier.
Having good crew is important at setup time.............
Good luck.