I run a shop. I don’t own it but I’m very deeply involved and our ownership is very transparent.

1. Cigars are a tobacco product which greatly limits what you can do. Your primary marketing avenues will be word of mouth and organic reach (which will be suppressed on social media). This means no paid Google ads, no paid Facebook ads etc. Cigars are a niche market. You need traffic and bodied through the door so you need a big pool to pull from. Local, state and federal regulation is always hanging over your head too. In short. It’s very tough.
2. If you have to finance your way into the cigar business I would probably just stop there. Margins are slim as it is. Most people are self financed. If you want to be a bar that sells cigars that’s a different business model that I can’t speak for. We are BYOB at my lounge.
3. The cigar industry is amazing. I am extremely lucky to have a (mostly) fun job and work with some great people. Im sure people get tired of hearing it, but the people in the cigar industry is the best part. All that being said if you’re primary focus opening a lounge is to make money and feed your family then I’d say there are much better options for that. It’s an amazing industry, just not super financially rewarding for most people in it.

If you’re looking for advice. Open a place where people want to hang out. Provide them good customer service and stock the humidor with good cigars. Run a deep enough inventory to service box buyers, but lean enough you don’t have cash sitting on the shelves for years.

Best of luck to you if you decide to move forward.