"If you are only going to move it once or twice, here is something to think about. In the ten years I have been hauling my boat around in Calif, Nevada, and Arizona, I have never been stopped or looked at funny by CHP."
While I understand this quote, here's something else to think about:
If you are illegally towing a large boat (or any boat, for that matter) and you have an accident that is even minimally related to the violation, two things will probably happen:
First, your insurance company will decline coverage as you were in violation of the policy--as in "the Secretary will disavow any knowledge of your actions." You'll be on the hook for EVERYTHING out of your own pocket.
Second, the accident will be blamed entirely on your "minimally related" violation. Juries like to assign blame where there is a clear violator/wrongdoer, and you will fit the bill.
What do I mean by "minimally related"? Well, if the accident is a sideswipe, unless your oversize load was marked EXACTLY in compliance with the law, you will be blamed, even if the other driver was "all over the road", talking on the cellphone, eating a burrito, combing their hair, and rattling a rattle at the kid in the backseat all at the same time. Why? Because the trooper investigating the accident can't testify to any of that--s/he will only be able to testify that one of your flags was in the wrong place.
Do you have the license required for this tow? If not, and the tow wavers from side to side and causes an accident, or you get into a jacknife situation, you will be blamed--because you hadn't demonstrated the skillset necessary to tow such a trailer in advance to the CHP. Again, this may be the only infraction that an accident can be hung on--and it will be.
Like I tell people who brag about the cops never patrolling the road they drive home on from the bar--getting busted by the cops isn't the worst thing that can happen. Being in an accident that kills a father of five young children when you aren't legally driving is--because it will wipe you out financially, if not emotionally.
The chances of your getting hit by a soccer mom distracted by a carload of screaming kids is always greater than zero. The question is, do you want to face that chance by doing something that would nearly automatically make you legally responsible for the accident?
By breaking the law, you're probably changing your whole legal position following the accident. If you were in compliance, you'd be arguing in civil court that "it wasn't my fault" and you'd have your insurance company lawyers to help. If you were breaking the law, not only will that be a tougher civil court argument with less help, you'll be arguing in criminal court that you didn't break the law with "gross negligence", because simple negligence only gets you a year in county jail. Gross negligence gets you two to six in the state pen.
Have fun choosing whether you abide by or break the law!
BTG
(PS--A similar scenario presents itself on any boat with 9 people on board but only 8 PFDs, no matter how close to shore you stay.)