Mike,

If I understand what you are doing, you rest the mast on the car to hold it high enough to help when you raise it. I have an H-16 and made a tripod that I set the mast on to hold it up when I raise it. That may be a way for you to hold the mast up (and turn the boat around on the trailer). I extend the jib halyard with a length of line and tie it off similar to what you describe, then pin the forestay. The tripod is 3 poles and some rope, not much to it.

Howard