I'm not sure on Illinois laws, but it seem regardless of the jurisdiction, that if I title isn't fully in ANYONE's name, he stands a snowflake's chance in hell of getting coverage from ANY Insurance company...especially if a claim should occur. My best thoughts would be, at least get the title work finished, say in a local friends name, somebody he can trust, somebody who is already insured. That way if, say it ever was sold, or a claim should occur, it would be easier to get any needed paperwork processed.
This scenario is just weird!