Here's a few idears I've formulated, mostly from dealing with my old sails, which became legendary on my beach,
To isolate your point of resistance, try shoving an inch or two of sail up the track, then pull on the halyard. If the resistance changes, clearly you've got feed issues. (Don't overdo the shoving, or you'll jam up right there and cover up any hypothetical feed problem.)
Does the sail hang up when you pull it down the pole? if not, suspect the headboard, because it rides differently when hauled by the halyard or pulled by the sail. It should come down somewhat easier in any case, with gravity on your side 'n all, but if if practically falls down the pole by comparison to hauling it up, that may tell you something
Is your headboard eye alligned with the masthead block? Pulling significantly off center, inwards or outwards, will tilt the headboard, increasing resistance.
Recently, Hobie shipped some brand new sails with new boats which had a problem. The bolt ropes had been cut in such a way as to mushroom ever so slightly right at the top end - one sailor we know used a hot screwdriver to "shave" his down, reporting good results.
Coating a bolt rope with McLube is more responsive to technique than apparant. It says right here on the can to coat lightly, let dry 15 mins, then repeat. Since the product claims to be a coating which congeals in 15 minutes, I infer the first coat mostly soaks in, the second mostly lays on. Most sailors I've seen spray it on once *as they feed in the sail* . Also, I spray each coat in three passes, so as to get the luff-to-boltrope transition on each side, and the middle of the bolt rope. I figure I can't coat all sides of a round bolt rope spraying from only one or two directions.
Overtightened battens will pucker the boltrope, causing resistance. Examine the bolt rope for marks indicating it's contacting undulyon any surface, near the battens. Check with the experts for your sail's ideal batten tension. Many newer sails need much less than the old Hobie 14-16 used to need. When you've got halyard hauling up, and gravity/general orneriness resisting you at the bottom, you're stretching the sail vertically. In many sails, this slightly tightens up the battens. That's why a little downhaul increases your draft, to a certain point, after which more downhaul is supposed to flatten. If your Battens are too tight, one symptom of this can be that you never can't seem to flatten by increasing downhaul. LIke I said, check with your sailmaker for the behavior they expect from properly tightened battens. while you're at it, unless they supplied the battens, ask them the initial bending loads, and max draft location. Picking up a 5 dollar fishing scale is worth it. I had to re-cut and re-taper some of mine. Got great improvement in performance.
Hope this helps!