Thank you for another group of evocative images, Mark.
It's interesting to consider what might have been, how many of those structures might have been saved or repurposed to better reflect the city's historic past. How fascinating it would be to step back in time to experience those buildings as they were. (Which is not to say many of them would have been attractive places to live or work. For example, consider the Roy Lohnes barber shop building at the corner of George and Lower Water; the businesses still operating despite the smashed windows and rotting siding above.)
I find it fascinating to ponder the names on the signage and reflect on the human stories they represent, largely lost to history. For example, even the modest parking lot sign in the last image you shared. It declares the place, now occupied roughly by the Law Courts, to be "Bedford Square", not a name I recognize at all.
Consider the Jas. Simmonds Hardware building, the structure at 1855 Upper Water, among the large group of buildings the city voted to expropriate in 1968 to make way for the Cogswell Street interchange. The company was established late in the 19th century by James Simmonds, who served as Dartmouth mayor from 1888-89. It appears to have operated for a time on Water Street (now Alderney Drive) in Dartmouth. I found old company material online that says they were distributors for Ramsay's paints and stains, made by the A. Ramsay and Son company at their factory in Montreal, also now all but forgotten. Did the firm simply fade out of existence after their building was acquired by the taxpayers; were their assets bought out by someone else? I can't say.
And then there is the Tobin's Rakwana Teas building, visible in the intriguing colour photo from 1956. According to the Dictionary of Canadian Biography, John Tobin was an Irish man who arrived in Halifax in the 1940s and established a general retail and wholesale business. He served a couple of terms in the pre-Confederation NS legislature before apparently shooting himself to death in 1869. But his firm carried on as prominent tea merchants, apparently until at least the late 50s. You can find images of their commemorative royal coronation tea tins online. I'm not sure of the company's fate but I did find a couple of obituaries for former Tobin employees that suggested they later moved to Morse's tea company, perhaps suggesting Morse absorbed Tobin at some point. Lost Cod Clothing company markets Tobin's Tea branded t-shirts. Rakwana, by the way, is a tea growing region of the former Ceylon.
Also intriguing to me is the Levine Bros. Clothing building (Rubbers Boots & Shoes). This company was apparently around for several decades; I located an entry in the list of investigations of the Halifax Police Department for 1932-33 that included the report: "Levine Bros. Clothing store Ferry Wharf. Reports of clothes stolen from hanger outside store. Brown with light pencil stripe, size 37." But I could find nothing else about this firm: who were the Levines; when did they open the business; where did they go after redevelopment took their building?
The buildings are interesting, but what preoccupies me is the human stories behind them, the people who occupied and visited those structures and gave them life. Stories that, for the most part, are lost to us, for now.