Since I'm not serving "2-Buck Chuck" but premium wines that are selected to pair perfectly with the menu I think it would be better to go with a higher quality cigar selection as well.
One of the things I get the most enjoyment from is sharing with friends and family something that is a cut above from what they are used to enjoying. Not necessarily more expensive, because I don't believe that better quality always comes with a higher price, but is a high quality item that may be overlooked by many. Especially when they think that what they've been enjoying, for as long as they can remember, is the "best thing out there". I can't tell you how many times I've served a food, wine, or cigar, where the first thing out their mouth is "this is the best I've EVER had!". That is truly enjoyable to me.
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