The Detroit Publishing picture above is titled “23rd and Fourth Ave., N.Y.” and the date is listed as circa 1908. It is almost certainly from that year, as shown by a building accidentally captured in the background.
First, orientation. The third building on the left side of the street running off to the right, directly above the woman in all white holding a white parasol, is the reasonably famous Church Missions House, on the southeast corner of 22nd Street and Fourth Avenue. (Fourth Avenue from 32nd Street to 17th Street was renamed Park Avenue South in 1959.) So the street to the right is Fourth Avenue, looking south, and the street to the left is 23rd Street, looking east.
Second, the accidental photobomb. A bit down Fourth Avenue, on the far right side of the photo, is a building where we can see through the windows to the sky, as if it’s in construction:

Note the window pattern: pairs of vertical rows of windows except at the corner, where there’s a single row, with arched windows at the top floor. The is the Parker Building, at Fourth Avenue and 19th Street, and it’s not in construction, it’s in demolition because it burned on January 10, 1908. Here’s the frontispiece of the forensic report:

Definitely the same building. The only difference between the two is the thing that looks vaguely like scaffold in the first picture:

That appears to be a debris chute held in place by heavy timbers, which would mean demolition of the top floor is in progress. Based on the clothing, this photo was taken in warm weather (warm enough to not wear jackets), some four months or more after the fire. The photos in the report were taken within a few weeks after the fire.
The exterior photos don’t really give a sense of the damage inside. Here, for example, is the forensic-report plan of the sixth floor:

All of the areas marked “I” had the tile-arch floors damaged by impact of debris to an extent that they were no longer salvageable. The various symbols around the columns (see columns 17, for example) represent failure of the column fireproofing. At some floors, the columns themselves were badly damaged; at some floors the collapsed areas were significantly larger.
The Parker Building fire was not a moment that shocked the design and construction world the way that the Darlington Apartments collapse of 1904 or the Triangle Fire of 1911 did. It was still a meaningful moment in the evolution of fire-proofing of steel-frame buildings in New York and it’s a bit weird to see it in the background of a picture of something else.
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