My guess is his gig is strictly contract work and not subject to benefits or any of the other perks that make full-time work for others more attractive than it might otherwise be.
I always considered Ray to be one of the two or three best writers at the paper and have seen his by-line occasionally as a freelancer since he left full-time employment as a sports writer, based in the New River Valley. His coverage for years of the Roanoke Valley Horse Show has always been exceptional and interesting, even to somebody like me who doesn't especially fancy horses.
I'm seeing a lot of by-lines these days in local media from former Times employees. In fact the Roanoke Regional Chamber of Commerce-sponsored Roanoke Business magazine is basically written by former RT employees, most of whom have full-time jobs now, but enjoy keeping their hand in the pot.
Cox's wife, Sarah, a long-time freelancer who was primarily affiliated with the RT, is now showing up in my former publication (co-owned with Tom Field), FRONT, among other places.