Ouch – dealing with the DMV (any State) can be a headache. I know that I’ve been frustrated a few times here in NJ, but nothing this difficult. Sounds like some research is in order as to the requirements…
Do you have any friends or local club members that may have experience with this? This particular forum is not very active, thus may not be the best place to look for answers. My 2 cents – I would suggest joining the Shelby Club forum (saacforum.com) and ask the same questions on there – a LOT more folks with a LOT of experience with old/collector cars, definitely some in VA. "Obviously" there are ways to get a replacement Title, some guidance is in order.
Good Luck.