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· Old enough to know better
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It hooks up fairly far back on the tiller and so it should be able to reach through a full swing. If it is just a touch off as Mike says it should be OK. They not only come off quickly, but can be (and should be) stored below. I have never actually used one but have tested on at the dock on a boat I looked at and it went from stop to stop. I have used wheel pilots and they are great even when not on a long trip as they free you to move around, either to single hand or even to go relieve yourself or get a cold beverage. Kind of one of those things that once you use it, you are like how did I ever get along without it?

The newer tiller pilots seem to not last long from what I have heard, if used a lot. Especially if you sail in rough weather or rain. It might be worth looking locally to see if you can get a used one to try out for a season or two, then keep it as a backup. I believe Cruising Lealea went though a few on there crossings but seem to do well with surgical rubber hose. Not sure how that would work on day sails where you might change direction several times. Generally completely self contained and should not take more than a couple of hours to install, even if you pot out the holes with epoxy as you should. Hardest part likely will be running the electric.
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