Hi Hack,

if you have checked your halyard pulley, sail track etc. and all is clean and running well. You might find some dry lube helpful, I have used silicon spray in the past and it helps, but have recently found Teflon spray works even better, just spraying bottom 1m of track has made it a lot easier.

But I have found it is technique and patiences as much as anything else, brute strength is not the answer. Keep the mast in line with the sail, if wind is blowing sail side to side it makes it much harder, also you can push most sails up a bit as well at each batten pocket, just don't rush it, this generally works for me.