I remember some of my high school trips for art/photography class to the Distillery District circa 2004-08. Back then the area felt like a complete island among the overall urban fabric of the east of downtown area, surrounded by oceans of parking lots. Condos eventually were constructed to help provide a gateway on the NW and eastern edges of the area, and retail improved within the historical spaces.
I'd say the popularity among the entire district has been quite meteoric throughout the entire 2010's decade, and that the romanticism of the area has been elevated to new heights. The boost has been two-pronged. Between the increased immediate residential population from the condos, and seasonal attractions of the Christmas Market and throughout the year. In turn, the popularity of the market has created a reciprocated appeal to the ownership of real estate of the area and retail tenants. The emergence of Pan-Am village and then into Canary District has further integrated the area into a more well rounded urban neighbourhood.