Sailor Jeff made a good point about the racheting style as not to overtighten but you own a Hunter 23 with a wing keel on the trailer. The only place of over doing it would be on the rub rail but having sold and trailered many of that model boats over the years, I strongly suggest the recheting style as the boat sits high on the trailer and the style you are asking about always slipped for me which is why I got away from them. Not sure why but it could be the length. The other smaller orange colored straps not good either. I suggest a yellow two inch strap long enough to go over the boat with the racheting style. Also, twist the strap on each side to keep it from slapping. Maybe it is the slapping on your strap causing it to become loose but either way, I would suggest highly the racheting style. If it is new, you might want to put a cloth down on each side where the strap comes over. After 20 miles, stop and pull over as a good precautionary thing to do to check all tie downs and wheel hub heat. You will have a little heat but if too hot, then you have bearing issues.
