Re: First time singlehanding, bad things happen, the sound of breaking fiberglass, et
I am really sorry to hear that your first single-handing effort did not go well. I know that has to be a little upsetting, but as others have said, at least no one was seriously hurt, and the other good news is that you are looking at this critically and trying to learn from what happened.
There is a couple things that I would suggest. First of all, I use a mix of strong points and jacklines to attach my tether. In my case I have been recycling old kevlar core halyards for jacklines but its easy enough to make jacklines out of webbing, s.s. cable, or low stretch lines. At least in the short run, these can be cleated to your bow and stern cleats and run down the side decks. I have spent time studying how to run my jacklines so that I can move the length of the boat without having to clip and unclip, and to minimize tripping hazzard. (In my case, when not in use, the jackline sit against the crease where the cabin sides meet the deck) Basically, the jackline needs to pass over all sheet leads and you should get in the habit of using the windward jackline and making sure there is slack in the lazy sheets before you leave the cockpit.
Practice using the saftely clip on the teather. Once you get used to it, you can use it one handed. It takes some practice figuring out how your specific clip works and where to grab it to allow it to work efficiently. (And they are all a little different so practice on your own will not assure the same efficiency on a different teather.)
In terms of tripping over your teather, there are tethers which have elastic in them that 'scrunch' up when not under tension. When scrunched the clip barely reaches the deck and so is less of a tripping hazzard. The factory made ones are pretty expensive and the elastic lasts maybe 6-8 years, so I have made a replacement using very heavy webbing and shock cord and the old hardware. (Don't make your own if you are not skilled at this kind of structrual hand worked stitching.)
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay