If he drives his vehicle for you, it is in your best interest to have insurance for non owned vehicles, to cover your butt. You could be in big trouble if he injures of kills someone while he is driving for you.
Search the topic of insurance here on the thinktank it will open your eyes to what you need. Here is an example:
Ours was cancelled a couple of years ago and it took us 6 months to get it replaced. We could get instant coverage for 100k a year or wait and get it for 30k. Being that we never had a claim so we rolled the dice and waited. Sure enough we had a driver use his moms car, get in an accident and his insurance denied his claim. The other guy sued me and I had to settle it out myself. All in all it cost me the same but did make for some sleepless nights being the attorney was trying to shake me down for 250k. I’m at the point where I’ll pay for the insurance and sleep at night.