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I've seen beautiful cigar bars in nice areas that never get any foot traffic and over priced places in low traffic spots do well. It's really on how you run the place and who you hire to work for you. If you go though with starting your own place, make people feel welcome. I'm sure your bartending experience will server you well in that regard. And, pay attention to the customers. Place I like to visit has such loud music/singer you can't even converse with the people at your table. It has discouraged me from going back as often as I would otherwise. The place tends to die down once the live band/singer get going. If it was just the guitar player I would be fine, in fact it would be perfect.

Anyway, as a cigar smoker you already know which areas are in need of a lounge, geographically speaking. I'm sure you'll do well, just do your homework on the current and pending legislation in your state/locality.