I'll answer a few things, and give some thoughts:
1st, to just get this out out of the way; If you have a helper who can "lift the mast/toss the mast upwards" from the bob the first few feet, there is almost no need for a GIN pole at all. The most difficult part of raising the mast is the "Dead-lift" from flat to resting on your shoulder. Once it's in that position, lifting it unassisted is a breeze. For security, run a dockline from the Forestay, around the fore-crossbeam, and back through a Cam-Jam on the main cross-beam.
Ok, now to directly answer your questions:
If setup well, the Jib/forestay will not be "attached", but rather resting atop the Gin pole. When the mas raises to about 45 degrees, the Gin pole will then fall harmlessly away, landing in the fwd tramp.
Tips to transition: A few things: on the forestay, add a dedicated shackle at the top-most hole on the adjustment plate, Use this shackle for your "lifting process", and it will leave the bottom of the plate unobstructed for when you attach and pin to the Furler.
There are a few ways to transition from the mast being supported by the lifting apparatus, to being hooked to the Furler. I think you'll learn your own method of getting this done easily once you try it. I suggest an intermediate pulley attached to the center of the foreword crossbeam, or as I do it, a line that loop from the forestay around the fwd crossbeam, and back to the cam-jam on the main crossbeam.
--- I'll explain how I do my mast Solo, and it might give you some ideas to help:
I run a thick dock line from the 'hoist' shackle on the forestay (connected by a basic carabiner). The line runs forward, then around the foreward crossbar, then back to the Cam-Jam cleat on the main cross beam.
I take 1 moment to assure all lines are clear of obstruction and that the mast will rise cleanly: Then I deadlift the mast vertical. Once the mast is totally upright, I reach down and pull tension onto this dockline, and then jam it into the cleat when it's tight. This holds the mast upright and allows me to get off the tramp and walk to the forestay.
Because I ran my 'hoisting dockline' around the front of the foreward crossbeam, the jib/Forestay is now exactly where it needs to be to connect the Furler with minimal effort. I connect the Furler, and once the cotter pin it secure, I can release the tension from the dockline. I jerk the dockline line out the cleat, and the mast is now fully supported and rigged by the standing rigging. I can remove the carabiner from the upper shackle, and then stow the dock line for later use.
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