I don't like the idea of adding 3 more pieces of equipment to my
rigging aids, but I bet that he can do it pretty quick.

I use Udo's dolly and only need a safety spotter over 25 knots or so.
I have them stand at the dolly, not at the tip.

I do rotate the wing to level, if you really crank down on the wing
clamp, then the wing doesn't move around.

One note about Udo's rig, get the lateral adjustment option, it really
improves rigging ease.

Todd Smith
3S