Congratulations, greeting from the England and welcome to the Hobie way of life
Been exactly in the same place you have been regarding hoisting sails, it was a real pita on my first H16 circa 80's.
It turned out there were a number of reasons that seemed to have caused this issue.
1) The sails were old and original as such the bolt rope had swollen this causes friction while hoisting,
2) The 80's mast track has a smaller sail feed section than that later models which can cause issues when hoisting, especially that last foot or two, see 3 (the track area that flares out that one feeds the sail into)
3) If your mainsail lower bolt rope is tight or jammed in the boom (as in my case) it can cause the sail to bind in the mast track due to the acute angle and tension, so ensure that outhaul is loose and the main can slide freely along the boom track.
4) Silicon dry lube (already mentioned in previous posts)
My cure in the end was that I picked up some second hand hardly used Hobie world sails on ebay and someone from the club gave me a later mast, the sail goes up like butter.
But I did test the new sails with the original mast and though slightly stiffer it hauled up just fine without little effort.
Also tested original sails in original mast they went up much easier once they had free movement in boom. But problem was the bolt ropes were shot so they continued to jam in boom track.
It's already been mentioned but defiantly agree upgrading those jib block will make a world of improvement and enjoyment particularly when out solo.
Continue to enjoy sailing her its the single most fun you can have
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