We've all been there, even on newer boats. In my case, I have no excuse, except for ignorance (aka "lessons learned")...

On the H16, there is a split tramp, so it's easy to tie a tow line to the crossbar. Of course, I used the dolphin striker once and it got bent.

On the H16, there are no "dead end" fittings (the kind that terminate in a thimble). They are all just wrapped around a stainless loop and use crimp connectors. Very easy to inspect for damage. Of course, one time, I had a broken wire and ignored it, dropped the mast in a regatta a few weeks later. I think this was caused by my storage "technique" (just wrap it up and tie it down).

So now, I am extremely careful about how my wires lie before securing them on the trailer. I avoid kinks, small-radius bends, etc. Basically, if the wire is fighting me, I stop and do it over until everything lies down nicely.

Mike