I really don't have much problem with mine, but there are some crucial things to remember:
footwear with excellent grip (I prefer bare feet)
a sturdy piece of foam rubber
trailer wheels locked into position
good balance
no powerlines above
First, place the foam rubber on the cuddy next to the partner hole.
Check to make sure nothinig is hung up on the mast (things you can't reach later). Check to see that your windex is on and secure!
I start on the ground and pick up the mast from the middle, then raise the head by wedging the foot on the ground and, hand over hand, bring the mast to vertical. Once the mast is vertical on the ground, make sure the stays are all hanging clear.
I manuever the vertical mast so it's just abeam the boat. At this point, I climb aboard, keeping the mast balanced with one hand (much easier than it sounds).
From deck, I can get ahold of the mast at mangeable points and hoist it aboard, making sure to keep it balanced and vertical. I carry the mast to the cuddy roof and set the foot down on the foam rubber.
At this point, I
could drop the foot straight down to the step.
(I
could, if I didn't have internal (infernal) halyards, which means I need a helper to fish the halyard tails through the cuddy hole and clear the way down under).
With the mast stepped, I find it stays put while I secure the shrouds and headstay.
When I got the boat, this process seemed daunting, but after practice, it's just not such a big deal.
Just watch those powerlines!
Cheers