Tough Question

[guado]

Let me eat lunch and I'll come back to this. To much thinking on an empty stomach is not healthy.

[JFellows]

Investing in cigars is just like investing in the stock market. If you can buy low and sell high, then go for it. I'm a capitalist by nature, so I say make a buck when you can. However, capitalism and philanthropy aren't mutually exclusive. I love giving away cigars (particularly if I have a bunch of the same cigar from a new batch, as it sounds like you do). There's nothing wrong with selling cigars to those who are fortunate enough to be able to afford them, and donating the rest to noobs/friends/those who are less fortunate.

[Shelby07]

I think if the person buying them is happy with the deal then it's a good one. The seller needs to do what he is comfortable with. Personally, I would not try to make a profit on them, but I am in a different place in my life than I was 35 years ago and there is no need to. At one time I couldn't afford to be generous, now I enjoy it.

As for trading - like for like. The sticks you are getting were probably bought at a discount.