+1 for the Tides track. I installed one on my 40.5 and the difference was amazing.Also, consider replacing the track with a Tides track. Makes a world of difference. We did and now we have to wear a hard hat when letting the sail down.
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On our '92 Hunter 33.5 the halyard does exit the mast about 6' or more above the deck, and the main raising method you describe is exactly how we do it.There is also technique... on masts with halyard exits above shoulder height hoisting by hand at the mast while a crew tails gives you much more result for your effort.. a big pull, tailer takes up slack, repeat... WAY faster too, an advantage again if you have lazy jacks..
Unfortunately this won't work nearly as well for you as I believe the hunter halyards exit at the deck level...
I have a roller furling main -- what I have noted on raising it once a year - SAILCOAT! for lube.Thank you everyone for your input and suggestions, one or all of them will fix this issue (I hope)
And make sure your main sheet is released because the boom will rise as the sail gets to the top.Here's an odd suggestion,, on my Hunter 30T, I had a similar issue,,
I couldn't get the main to the very top of the mast - check your reefing lines,,,