Tom-
I have front cradles on my trailer to support the boat as I slide it forward (by picking the boat up at the stern, wheels and all and pushing forward until wheels "seat" into their "L" angled spots, then go forward and lift front beam into their "slots"- this puts the hulls above the front cradles slightly. Then the rear mast support is pinned in (this traps the wheels down) and the wheel ties loosened so a line is then used to slightly lift the rear beam into contact with an inverted "L" angle where the beam is lashed into place. Again, the boat is now entirely supported by 3 points so the trailer can pretty much flex all it wants (actually the front beam support is quite substantial and flexes very little) and none of this flexure is transferred to the boat.
Loading the boat on the trailer can all be done with the spi pole in place IF the front mast support is far enough in front of the front beam supports that the boat gets seated in the slots before the spi pole hits the mast support. This is NOT the case on my trailer so I take pole off before loading the boat. Alternatively you could have a swing away or pinned front mast support that would be removed/folded down while loading the boat.
Would love to go to Island Hop- When is it?

Kirt