People are talking about being embarassed by a woman, I guess they should have seen you manuever that 650 winding around at Holiday Isle two years ago and pull out the OSO Cig. I seem to remember many experienced male drivers staring in awe with their mouths hanging open in disbelief and saying they would never of even tried back in there.
I have a few questions about this situation though:
First is this the same Frank that did some hauling for Hideaway?
Second, people often confuse cargo insurance and liability insurance, they are very different.
And finally, trailers are complicated, it depends if it is your trailer being towen behind your truck, if the trailer is in a company name, and each of these effects coverage. If the trailer swings around and hits something that falls under the liability coverage but the damage to what is on the trailer is totally different as is theft.
The point is if you are letting someone else haul your boat, you better look into it very carefully first. If this Frank guy was any type of legit regardless of his cargo insurance limit or lack therof he should be bonded and have enought coverage to pay for the trailer. Anyway just my 2 cents.