Pete,
I agree with you on the issue of waisting time walking back and forth. So everything that is needed to rig the boat goes in the trailer box and nothing else.
The boat slides off the trailer and is positioned so the bow is within 2 inches of the trailer.
This is neaded so I can use the trailer mast supports to help put the mast up over the bows. The sidestays are even attached to the chainplates while standing in front of the front beam.
The main sail comes out and goes up. The boom and the C/Bs come out and then I have to walk out between the boat and trailer to attach the rudders and mainsheet system.
Up to now I've not walked more than 8 feet at any one time.
Then I move the boat back far enough to rig the spinnaker setup.
Just the way I have approached the same problem.

Regards,
Phill

I know that the voices in my head aint real,
but they have some pretty good ideas.
There is no such thing as a quick fix and I've never had free lunch!