My experience from the TA last year isn't too much help because we went W-E, but I am familiar with the Virginia area so I will comment anyway.
There is some luck of the draw there. Weather is likely to be OK, but it is a bit of a gamble. You will need to be ready for cold and wet weather, snow isn't impossible, but you have a good chance of avoiding it. Will you have the option to push back the start at the last minute if it looks awful?
I wouldn't sweat the personal safety issues especially in remote areas. We were amazed how nice just about everyone we met was. People were almost universally kind and generous.
Any risk we felt was more from traffic than anything else, but we found the route to be OK in that regard too. The most aggressive drivers were on what will be your first day or two, but overall we felt pretty safe.