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If you're expecting to make it easier to tail the jibsheet by buying bigger, more expensive winches, you'll be disappointed. If you're finding it difficult to grind in the jibsheet, the problem isn't with your properly functioning winches. Your existing winches are two speed, and they provide all the power you should need to tail a jibsheet.

The problem lies mostly in helmsmanship. Whenever you or your crew are having to grind long and hard with the winch handle to tail a jibsheet, the reason is because the helmsman turned the boat too far during the tack. The remedy is to stop the turn when the jib is streaming along the gunwale on the new tack. At that time, the jib is not loaded, the sheet is loose and all but about 3-5 ft. of it can be pulled in by hand, without using the winch handle. Since only a few feet of line remain to be ground in, you don't need self tailers. You can hold the sheet with one hand and grind the winch with the other. Since the sail isn't loaded, it's easy to grind the winch. When the sail is nearly in trim, the helmsman should bear off and load up the sail. That little amount of fullness will be just the right amount to help the boat accelerate out of the tack.

I should add that, before you start the tack, put the winch handle in the winch and put 2-3 wraps of line on the winch. If you wait until after you have tailed the jib on the new tack, you'll waste too much time fumbling with the winch handle to insert it into the winch with one hand.

The boat's designer prescribed a winch size suitable for the boat. If you're having difficulty tacking, it's almost certainly a matter of technique.
 
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