I think it's okay, especially if we know the person we're sending to will enjoy it (like in a MAW). Plus, life's too short to even think about it, really. I mean, we all have a lot of similar cigars and will have sent and received a lot of the same things. How many bombs, passes and trades have UCs, HEs or Short Storys? I'd never want someone to feel they have to suffer through a cigar they don't like, or have it sit forever neglected in a humi, just because I sent it to them. Better to pass it on to someone who might enjoy it.
You could always start a re-gift pass.