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We can try pulling the turning block back further. The jib is not as flat as I think you are suggesting we try.
Not sure I can answer the question of which sail luffs first when we are heading up, but trying to recall back I think it is usually the jib.
The jib is furling. We can shorten it up quite easily and we can try that. My assessment of the sails is that the main is probably average condition. It isn't a tee shirt, but it is not as stiff as newer sails I have seen. The jib itself is probably closer to the tee shirt you describe.