Also not a local but was in the area a few years ago visiting a friend in the area. Check out Prime Cigar in the Brickell neighborhood. When I went, they had a solid humidor and bar, chill but sophisticated space, and live music. It's one of the places I use as a standard when judging lounges. And I've been to multiple Casa de Monte Cristo lounges, including the one at Caesars in Vegas.
Also, if you've got time, check out Wynwood Walls in the Wynwood neighborhood. There's also at least 1 bar/club in Little Havana that has an outdoor stage with live music and the bartenders sell cigars that you can smoke while enjoying some good vibes.