My .02 I don't care how far I am traveling rather its 5 miles to the ramp or to the Keys. The boat is strapped down both at the stern and the bow. When travelling at distance I take a tool box to fix most issues. Extra jacks and 4x6 blocks along with just about everything else that others have listed. But a hard lesson learned a few years ago right in the intersection of 1 and 1A in the Keys. I lost a tire and rim when it snapped off. It took a whole day just to find the correct studs to replace the broken ones. So maybe a half a dozen wheel studs.