Considering hiring an idependent contractor to assist painting the exterior of my home...he doesnot carry insurance?

I am not admitted in Colorado.  I would not hire him.  Check your homeowners policy but I doubt that he would be covered.  If he gets hurt he is going to sue you, no matter what you write down.  In fact, if he has people helping him you should ask him to add you as an additional insured on his policy to make sure you don't get sued by them (they can not sue their employer as they are limited to Workers Comp).  The bucks you save are not worth the chance you take.