Congrats on a purchase I feel you will not regret.
The tall rig is really only 2 feet more than a standard. On ours, a standard, the main was very difficult to bring to the top. I (mistakenly) put lithium grease in the track on the mast and on the guides attached to the sail. This made a mess as the greasy aluminum oxide got all over the sail.
It did however help in getting the main up all the way. But that was last season. This season I cleaned the sail guides and as much of the mast groove as possible. I then used WD-40 which also is not recommended, but it has worked well and has not stained my sails. I also learned that winching from the cockpit is a lot more difficult than pulling the halyard at the mast before it turns in the blocks at the deck to go to the winch. There is a lot of drag between the winch and the top of the sail on mine and I am suggesting that you may have a similar problem. Have you tried pulling the main up from the mast where the halyard goes up while your mate takes up slack with the winch? It sure seemed to me that the hardest was that last foot and I'm sure it's just from too much drag in the hauling components.
The tall rig is really only 2 feet more than a standard. On ours, a standard, the main was very difficult to bring to the top. I (mistakenly) put lithium grease in the track on the mast and on the guides attached to the sail. This made a mess as the greasy aluminum oxide got all over the sail.
It did however help in getting the main up all the way. But that was last season. This season I cleaned the sail guides and as much of the mast groove as possible. I then used WD-40 which also is not recommended, but it has worked well and has not stained my sails. I also learned that winching from the cockpit is a lot more difficult than pulling the halyard at the mast before it turns in the blocks at the deck to go to the winch. There is a lot of drag between the winch and the top of the sail on mine and I am suggesting that you may have a similar problem. Have you tried pulling the main up from the mast where the halyard goes up while your mate takes up slack with the winch? It sure seemed to me that the hardest was that last foot and I'm sure it's just from too much drag in the hauling components.