Stepping the Hobie getaway mask from a trailer

This year I did it much easier so I thought I would share. I used a winch on the trailer and a 10-ft ladder. The jib shackle is attached to a plate shackle to the winch. You attach the shrouds on each side and have the mast ready to step. Raise the mass part way with one person and help rest it on the 10-ft ladder in back of the boat that makes it easy for the one person to hold. The other person can then run around and start using the winch to help while the second person walks up the mast. Then all you have to do is steady the mast while the jib stay is attached to the plate and disconnecting the winch, and the side shrouds are tightened. Not only was it faster and easier, but it was obviously more safe. I have not yet figured out if I can do this one person safely.

only thing I'm wondering about is it seems the jib and forestay on the winch will want to pull the mast up straight, not rotated around.
Was this a problem for you? How did you keep it rotated going up? Sounds good otherwise!

We rotated it first and rested it on the ladder at the stern. Then winches and walked it up

I hope to post more, and with pictures when I have some time!
A quick note - I did try this. It works.

The 10' stepladder idea was good, I tried with my 8' ladder and found that really did make it easier to go up from there.

What I wound up doing was adding a 6' 2x2 galvanized tube on the back of my trailer (I had to extend the trailer to go all the way to the rear of boat).
Inside this tube, I inserted a 1.5" x 1.5" 4' galvanized tube with a roller on top. It also has 6" "guardrails" on both sides of the roller to keep mast from falling off.

Now, how high could I raise that inner tube so I could still lift the mast on to the roller? I found by standing in the middle of the tramp, I could raise inner tube something like 2.5' for a total of about 8.5' of a mast support to bottom of roller.
When you stand more towards front of boat, you can raise the top of mast pretty high when its light weight in the traveling position (before you push it back so you can mount on ball).

Once you get the top of mast on the roller, you can walk it back single handed and drop the base on the mast ball. So now, the mast is sitting at quite an angle before you do any lifting.

Then, I went all the way, I connected the jib/forestay to the winch and had my crew crank it right up as I held the mast in the correct position and walked it up with the winch.
Best mast raising ever! Same for lowering it. The cranking is super easy.

There are more details which I hope to cover soon. Only snag I hit was when I pushed the part of the mast where stays all connect over the roller. You have to be careful to keep the stays facing up so as not to bend those fittings.
It also may be that I should bungy the stays straight down the mast first as well, I will test this. I'm also about to change my 5" roller to a 6" roller to try to make it wider for the stays. Other than that, all is smooth and the operation is quick.

It also helps keep the mast out of the water when I have to raise the mast while inclined on a ramp. My crew didn't enjoy doing that the old way.

more to come...