I always raise the main first. I don't like the jib clew smacking me in the back of the head while I work on the main.
You can even use a quarter in the cup as a bearing. Best to get something in there so the base and cup don't wear and the mast rotates easily. Teflon is best and it conforms to the cup shape easily. The jib halyard tension can cause rotation problems as well. You should tension the halyard enough to keep the jib / forestay from sagging while going upwind, but the main sheet tension does this as well, so too much tension is not needed. Just make the shrouds taunt while sitting on the beach. Some sailors even sail the rig loose in higher wind to help depower, so what is the right tension? There is none, but I like the rig to be snug when I sheet out so it doesn't bang around.
The gooseneck would slide easier with a bearing kit added. They are standard now. You can see it in the catalog on page 39. The downhaul line should be 3:1. Tied off on the gooseneck, run to the cleat and back up to the gooseneck ring and back to the cleat. Tension the mainsheet to more easily downhaul.
Mast rake? Loosen the jib halyard. Move the shrouds to lower holes in the adjusters and re-tension the halyard. Repeat till you get it aft enough to nearly "two block" when the halyard is tight and mainsheet is as tight as you would likely sheet that day.
Yep, cut the jib battens short as possible while allowing for tensioning. You can also tape over the cap from one side of the sail to the other.
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