Personal Auto - Towing Another Car

I have a personal lines client who's a career mechanic & he also fixes cars on the side. He says about 12x/year he'll take his truck (and his trailer..) and pickup vehicles...tow them back to his house & fix them.

1.) I'm about 100% positive if something happens to the car on his trailer, his insurance won't cover that.

2.) Since physical damage follows the car, would the insurance company of the person who owns the car on his trailer provide collision if he crashes/

3.) If that company comes back to our insured, again...his carrier would deny it right?
Source of insurance-forums.net

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