I pay a premium for "almost impossible to find cigars I like" all the time, and I'm happy to pay it. If a guy has had a box of smokes in his care for 10 years, it has definately cost him something quantifiable to store them correctly and keep them nice for me to smoke.
If he paid five bucks a stick ten years ago, I'm more than happy to pay 10 bucks a stick now, and I think that's a bargain.