I've done Flagpole many times, it's my go to trail for a day trip when everything else is closed. If you go up Union Springs trail, you'll hit the staircase, which is the most challenging thing there, but it's still not anywhere near the level of what you'll find at Chaos or Gore (Big Dogs)...
OK, nope, not familiar with that one, Thought it might have been Steve who had Jeeps Xtreme, that was a great shop, but he closed it up a few years ago...
Wouldn't surprise me if the pic is a real vehicle. Google 'Cadillac Flower Truck'. They aren't super common, but Hearse manufacturers make a few of them every year..
As LostWoods stated, most all the legal wheeling close to NoVa is along I81 in the National Forest, there are also a couple Private Parks near Winchester, Chaos ORP near Capon Bridge, WV and Bigdogs Offroad events at The Cove Campground in gore, there are a few Parks in Southern PA too, Rausch...