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Since the topic of your post is ways to reduce rigging time, I will say that raising the mast manually (with one or two people) is the fastest way and it can be done safely.
Very true. I am probably way over cautious on this one. My ten year old daughter was working the winch as I guided the mast up when it occurred to me what was possible and I made her move away immediately. I lowered it and rigged the harnesses before I tried it again. Now I work the winch and stop to adjust the side harnesses as needed. Using the trap wires will eliminate the side harnesses and the bottom one goes on and off pretty quickly.
I use the other two trap wires in tandem to raise the mast so I don't have to disconnect the winch until the fore-stay is secure.
Leaving everything connected while trailering saves time but is there a good way to secure and organize them while the mast is in the cradle and the lines are slack?
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All of the cast components on the mast step are aluminum. I don't think that the mast step hinge is "engineered to break" per se, it just happens to be the weakest component in the base system, so it's the piece most likely to fail.
The hinge is a lot softer alloy than the base and the way I've heard engineers and mechanics talk about metallurgy and design in cars it wouldn't surprise me if it was planned that way. The hinge is much cheaper and easier to replace than the base would be. Seems like a good idea even if unintentional!