on the sewing side, the needle not punching through is telling you to have a think just how thick you want some areas.
i have broken dozens of needles on my machine and am coming to know what types of webbing ,monofilms etc not to sew.
try stepping back and trialing some test pieces of your sail cloths to see how many layers you can sew with what is effectively an unsuitable machine. , do you need great chunks of webbing in these light duty sails?
every time your machine stops with a clunk , your timing will slip slightly , till you need to reset it , so you will need to have somebody who knows how instruct you how to do it . I have had to retime my machine 3 times on one sail before

learning to do it gives you a much greater appreciation of what you are doing

for me , it has been one of the highlights of building my own stuff

on the sail recutting side, the last thing you want is a flat sail., you just want to recut the sail to make it flatter than one would normally use for windsurfing.
Aus 230 currently is being troubled by a 4m tushingham that is already too flat for a landyacht

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today i rigged a 3.8 recut from an old rushwind sail that is the fullest sail Ive ever had, and in a light wind it was a ripper, very stable and one of the best sails ive had for a while for keeping on 2 wheels, whilst still being fast.