One of the first things I do when scouting a city/market is to locate the people that actually make the "cool" areas cool.
The person that crafted the organic blueberry shrub for your $25 drink likely doesn't live in the area they work. Most of the time, they're accessing the same caliber of drinks and food but aren't paying the same rates.
From my experience in New Orleans, the young entrepreneurs, bartenders, servers, bar backs, hostesses, performers, musicians, you name it, don't live in the areas that are widely known as "cool" (yet).
Instead, they're concentrated in a handful of neighborhoods, which are cheaper by nature, inclusive, and provide a communal feel for those within it. Their current job is likely just a way to pay the bills while they pursue that other passion. Whether that's music, cooking, a start-up- you get it.
These are also the areas where these entrepreneurs/creatives can take their first leap.
Whether that's opening the coffee shop of their dreams or a vintage clothing store, the owners in these areas are willing to take a bet on a first time operator and provide cheaper rates (naturally, bc of less desirable real estate).
The creative mind behind the really cool cocktail menu or venue is also molding the neighborhood in which they live, year over year (just like the other residents).
Over time, these areas can become hubs for incredible cuisine, art, nightlife, and ultimately become widely known as "cool."
The fun part is finding these neighborhoods during the transitional period (careful not to be "too" early), witnessing the creative forces carve out what they hope to see within it, and contributing to the progress through strategic investments that will serve the community for years to come.
Once they're "cool", pricing power will naturally come into the equation and the next generation of these creatives will find another area to ultimately make their own.
Very much of the Richard Florida school of thought but a natural process I continue to seek out and track within our target markets.