That is funny cause I just said to my wife/crew yesterday.... "Think I'll play with the mast rake next."
On the mast stepping,... After turning the mast on it's side and setting the pin in I usually swivel the mast to one side till the port shroud is taunt and then I have something to pull against. I can't picture exactly what you are doing right off with the trap lines but I promise to stand out at the boat and visualize it tomorrow as well. Always looking for a new idea. Especially if it adds to safety. I do like the idea of bring the mast up straight down the middle of the boat since it would make the winch mounted on the post load better than it does with my off to the side method. I'm very interested in anything that shortens set-up time as well. I find the attention span of my crew tends to wander. I'm thinking of setting up a fixed schedule of tasks and who they are assigned to (similar to a pre-flight airplane pilot checklist). Seems we always have either someone standing around waiting for orders or missing a step. Probably by October we'll have it down just to put it away for winter.
I starting thinking about utilizing an old electric winch I have lying around here and mounting it (not permanently) on the rear bar of my trailer then running a line attached to the winch under the trailer up to a block at the base of the post on the trailer (that holds the mast up while traveling), up that post to a block and then attach it to the forestay. The beauty of the electric winch is a long remote control that would let me steady the mast and lift it all from the back of the trailer. I could then walk right up with it and using a little aluminum ladder I find handy to get onto the tramp. I also love the tip I read on this forum a while back about attaching the job halyard to a shackle on the bridle to take the weight off the forestay and let you attach the forestay to the bridle without having to hold everything up in the air while you pull on the forestay and slip a pin and a ring clip on. That is a great step to add to the procedure.
Great to talk to you about this though. Thanks for the email. Feel free to email direct at Gregoryhill@verizon.net anytime.

Greg