This may be as much an additional side-mystery as any sort of help in narrowing down the date, but the Boznu's sign in the lower left corner of the photo would seem to have some direct connection to this token, but the address is for the other side of the street. Photos from that side of the street show Delmonico Restaurant at that address, which matches with the other name on the token. One reading of the token could be that Joe Boznu operated a newsstand out the Delmonico restaurant. If that is the case, it looks like he took his business across the street at some point. A city directory might be able to say if that move happened after 1937.
 

In looking over all the rich detail in the photos that Gina linked to, I realized that I had missed something rather obvious in the original mystery of the mystery photo. That photo is from somewhere between 1937 and 1941 based on the buildings, but the answer to the exact year is likely to be found not in the details of the buildings, but of the street. 

Duluth replaced its streetcars with buses in the 1930s, with the last streetcar running in 1939, right in the middle of the year range for the photo. I asked my friend Jonathan Kibrick (I promised him I’d give him credit in my post) who has a rather encyclopedic knowledge of the technical details of transit systems to look at the photo and he immediately noticed two things.

The first is very specific: the two small objects on the wire in the bottom of the photo belong to the overhead contact system of a trolley bus using an Ohio Brass standard insulator set on a stringer with a 2-foot mid-span spreader bar and there is no wiring visible for a streetcar. This overhead contact system is more visible in this photo of the WEBC building from 1942. This means that when the mystery photo was taken the streetcars had already been replaced by trolley buses. A photo taken in 1940 from the end of the block shows one of these trolley buses.

Streetcar service in Duluth was discontinued in 1939, but looking at my Twin Ports by Trolley book it seems that Superior Street may have changed from streetcar to trolley bus with the conversion of the Lester Park line in 1934. A lot of different lines ran along Superior Street, however, so I’m not sure that 1934 was the last year of all Superior Street streetcar service. If it was, it only means the photo is from after 1934, which we already knew. 

His second observation seems to be more useful. There appear to be parking meters on both sides of the street. The world’s first parking meter was installed in Oklahoma in 1935. Minneapolis installed its first parking meter five years later in 1940. In Duluth, a photo of First Street in 1940 shows parking meters but a photo of the same street in May of 1938 shows no meters, although tear gas is obscuring the end of the street. 

If parking meters came to Duluth at the same time as Minneapolis, that would shorten the possible time range of the photo to 1940-1941. A better understanding of when streetcar service ended on Superior Street might confirm that.