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
. 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.