I side with the no-no group. I don’t like the combination of wine and cigars at all. Hard liquor (aged rum, cognac, whiskey all work for me) or even a drink are fine. I have been enjoying a negroni with cigars recently and the tobacco doesn’t seem to ruin the drink’s flavors.
I tired wine and cigars and while some I found to be not that bad, most of the time I found it to be a waste of good wine and went back to scotch.
It is a waste of good wine that deserves contemplation and attention, but not really a waste of okay wine, or finishing off the wine that was already open from earlier. At least in my opinion. If the three of you open a Turley Juvenile zin or Qupe Syrah or T Vine Petite Sirah after dinner with your cigar, those wines not have died in vain.
The only wines I like with a cigar are fortified wines as they seem to stand up to the cigar better. I have attended a wine & cigar tasting but found I couldn’t really appreciate the wines I tried. My favorite accompaniment to a cigar tends to be Wild Turkey American Honey on the rocks, a great combo with a cigar. 