This is all very funny, and I can see it is burning up the spare time of many here.
Given that, I really like the abstract logo that would make people think, and then ask about it. What better way to start a conversation with potential new members? I'm not enough of an artsy guy to be able to do it, but I'll throw some stuff on the wall and see if it sticks:
Poe logo is cool. How about somehow combining the RVA cleverly with a black RAVEN? I like this in particular because Poe has history in both Richmond and Petersburg. River, Raven, RVa. There has got to be a great combination in there somewhere.
The James and the Appomattox connect the area. How about twin rivers theme? Both Richmond and Petersburg are on the fall lines of both rivers. Falls guys? Taking a fall? I know, not very strong.
The James connects the entire state from Monterey to Va Beach, and is close to all the best roads we talk about (nickle and dime, Scotsville ferry, etc). With apologies to Joe Walsh, what about the James River Gang or a version thereof? Maybe a stylized JRG overlaid onto the outline of Va boundaries?
That all said, a very wise man whom I've always admired once exclaimed, "I don't want to belong to any club that would have me as a member"
Not sure we need a logo, or t-shirts, or decals, especially involving eating. The Wingers have been derisively described for years as the group that instead of "Lives to Ride, they "Ride to Eat". Is that what we want to be known for? Just sayin....