It's fun to try and pin down the spot from which this photo was taken (click for larger images). To begin with, the legends written on this photo read, from left to right,
High School (now Cross Street Village)
River Street
Deubel Mill (demolished)
Follett House (still part of Depot Town)
M.C.R.R. Depot (demolished, mostly)
Thompson Building (burned)
Now then. The big building at far left (labeled "A")...hmm, there are two possibilities on the 1895 plat map, above; the large building at left ("A") and the smaller one labeled "School." But the building in the photo is right up against the street, whereas the school seems to be set back a bit. On the other hand, there appears to be more land in the photo between the big building and the tracks than there is indicated on the plat map. Hmm. Gonna guess that the road most prominent in the photo, right next to the farmyard, is Grove.
The fenced area in the photo ("B")---is that the old Gilbert property?
In the background is an odd-shaped building ("C") that I'm guessing is the now-vanished railroad roundhouse. Do you think so?
Another complication is that if the visible street is Grove, the photo's foreground farmyard appears on the plat map not as a big plot but subdivided into several tiny lots. It's possible that the farmer in question bought several of these lots for his little farmyard, but it seems more likely that it would be shown on the plat map as one bigger property, like the "Gage, Est." property at the southeast corner of the tracks and Prospect.
I'm not sure. What do you think?
There are some amazing sleuths out there; my hat is off to you. No sooner had I posted this than one eagle-eyed reader ID'd the big building: it is part of the modern building of Marsh Plating on Grove! Check it out!
You can even see this old section on Google Maps; the staggered roof line gives it away:
You can see on that map that SOS Community Services currently occupies the site of the old cruciform 5th Ward school building, which seems to have been demolished.
Take a gander at what Joe said: "I think the picture was taken at about Prospect [as cmadler said also] and Congress. It also looks like it was taken from atop a building. I would guess maybe the 5th ward school."
Looks as though that was the only high point around, on the old plat map. Folks, I think we've figgered this out: this is a photo taken from atop the old 5th Ward school, looking northwest towards Depot Town. You guys are amazing! Thank you!
