As you noted, pricing aged cigars is speculative. When I seek to thin out my inventory my goal is to not try and screw fellow b/sotl. I look at current prices and then discount 10-15% adding on shipping cost. Yeah, I sell at a loss which is why I don't own a smoke shop. I see it as a win-win in that cigars I won't get around to smoking are enjoyed by someone else and I get a few bucks and additional space in my humidors.
Not saying that it's wrong to make a few bucks or to cover your cost. Just not my approach..
You have some nice smokes there. Enjoy!
c3s