I've smoked plenty of cigars in my life, but I haven't been a huge advocate. But I will claim that all of the
tobacco flavors I've tried taste like hell. HOWEVER, I did rather enjoy a Kona 2 flavor and was highly attracted to the coffee flavors (not all). i felt they had a better flavor that was more palatable. I really enjoyed a cheap cheroot from time to time too, so I could imagine adding a hint of cherry to a dark coffee flavor might make things taste better versus the cigar flavors imitating the cheroot.
Cigars tastes depends on how I would smoke it. Always with matches. Slow puffs, few and far apart to make sure it burns as slow as possible and not to dry out the
tobacco and become harsh. I also rarely inhaled smoke, when I did it was very very minuet amounts. Imitating that is never going to work and i refuse to buy tobacco flavors because I'd rather taste watermelon-lemonade than a fake tobacco that tastes like a stale black-n-mild underwater. It's nearly impossible to emulate the burnt smoke flavor, just like how it's hard to mimic a pecan-smoked tenderloin by adding flavor sauces and putting it in the oven.
I'm sure someone got the flavor right somewhere... but try a Kona blend or something like that. It's not a bad alternative to the tobacco flavors.