Mast Stepping

A few weeks ago I broke a toe while on vacation with my Getaway This didn't keep me from sailing with my wife, but when it came time to put the boat back on the trailer, I realized that she wouldn't be able to lower the mast. I was eventually able to do it myself, and this got me thinking about some mechanical help to step and unstep the mast.

I rigged a winch on the trailer's forwad mast support, installed a couple of SS eystraps riveted on the wing's support tube (to rig trap wires and give lateral stability while raising the mast). But I can't figure what best to use as guy wire to pull the mast up.

The obvious is to use the forestay. However, the mast is supposed to be on its side while being raised. If I use the forestay, the pull will rotate the mast in a fore-aft position (same with using the main halyard, and I'm not sure the halyard would be strong enough for the load). In fact the EZ Step info states "Works best with mast that don't need to be turned to the side for stepping."

Before I investigate complex rigging to keep the mast up sideways while being pulled up, does anyone know how critical it is for the mast to be sideways? Is anything likely to break if I pull the mast up using the forestay?

Bonus question: The part that puts the most stress on the stepping rigging is the first few degrees of lift. The tip of my mast support is at the minimum recommended 30' above the mast step, but any increase of the angle between the mast and the guy wire will help. Has anyone devised some support to raise the mast from the aft crossbar?

Yes, it is very important to keep your mast rotated 90 degrees. There are slots on the mast base which allow you to lower it. These slots are found on each side.

I run the standard winch strap under the trailer arm and then back up to the bow crossbar. I then winch it down until the bow is about 1ft lower than the stern. Then it isn't hard for me to stand on the rear of the tramp and lift the mast into place and if it's not raked too much then it will stay there while you pin it. I'm sure there are easier ways, but I'm still new...........

That's what I figured, but then there is no practical way to winch the mast up. Whether I use the forestay or the main halyard, the mast will rotate.

I just bought a sail slug that fits the main track, and will try rigging a loop around the mast attached to a slug with the two trap wires to keep the mast in the appropriate sideways position, but I was hoping there was an easier way.