Since you're here at the site a few day less than me, I'm entitled to say "welcome".
I'm not very conversent on the insurance industry so my comment is limited that which I know. You'd perhaps be surprised to know that a great many folks who enter the expedite industry do so without any trucking experience. Many of those have retired from other disciplines and are your age or greater; many in their 60/70's. Typically, we're all independent contractors or non-employee drivers of independent contractors. Consequently we have our own vehicle and health insurance or we are part of a group plan made available, at a cost, by their company or their owner. Enjoy the site, absorb the info and you'll do well but don't settle for low wage