I'm Proud of you Amigo....
Ya just gotta practice doin it in the wind now....You past your first test now just do it again and again until your mind will be focused on exactly what you want the canoe to do....
While you're walking with it over your head and arms stiff,practice lowering the Yoke down onto the back of your neck and walking around a tree or sompthin in the yard....turn and go to the vehicle and get upside the vehicle,squat just aliddle bit like a weight lifter and push up to get your arms straight above you,
ya might have ta rebalance before it slams you to the ground but remember ....you can do do this; just keep as calm as you can and focus on where the gunnels are gonna land on the rack.
Even on a van just get you a large milk crate, the yoke will be on your shoulders,walk up to the crate step up on it gain your balance, raise the canoe above your head and set the gunnel up and over to the rack.
This can be done even in the wind. Just hang on tight.
I always wore a pair of "WET"leather gloves with the finger-tips cut off.
You can do it. canoe needs to be empty by the way!
Keep us posted on your progress....Just Focus