Since you have trouble both setting and striking the sail it seems that merely increasing the stress on the luff is not a very complete answer. You report that lubing helps in a temporary way. So, make it permanent as one boat I've seen did by making a lube wicking slug that rides above the boltrope. Just wet it with silicone every week or so and it'll lube the slot each up and down.
How much of an angle must the boltrope go through to get into the slot? This could be the problem. If the slot entry is well above the boom, maybe you can fabricate a hanging guide that gets the boltrope halfway from where it rolls off the boom to the slot entrance.
G'luck
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