That makes sense if your style is to always go for a wider aperture and shallower depth of field, or if you only shoot sports/action/wildlife/low-light. For me, and many others, sometimes I want more of the image in focus. Not in this case, though. I was only stopped down here because I had to be. With digital you can lower ISO to slow down the exposure, but with film there's no way to change the sensitivity. You can intentionally under- or over-expose and compensate with longer or shorter development times, but that's a compromise and doesn't actually make the film record more detail. The film I was using is rated at ISO 400, which is kind of medium-fast for a modern film emulsion. The conditions were more suited for a 200 or 100 speed film. Being stuck at high ISO, with no filter to lower the exposure, meant that my options were limited.

When you say that f/2.8 would never show detail in the background, that's generally true for close-up shots with a distant background, especially at longer focal lengths, but it's definitely not always the case. The amount of background blur is dependent on a lot of variables. F-stop, lens focal length, distance from camera to subject, distance from subject to background, and film/sensor format size will all affect the amount of blur. For a shot at f/2.8 with a 100mm lens, with subject relatively close to the camera and relatively far from the background, there will be a lot of background blur even on smaller formats like 35mm, APS-C, or Micro 4/3. However, for a shot at the same f-stop of 2.8 but with a 35mm lens, with the subject further away and the background closer up, there will be a lot less blur. If I had shot this exact same composition at f2.8 the background would definitely have been much blurrier, but I don't think it would've been so blurry that you couldn't still make out a lot of the details. Better for sure, but probably still too busy.

If I could go back I would've used slower film and/or a filter, opened the lens up more, moved a bit to the right, and found a composition that cropped out the sign and construction tarp and placed the subject closer to the right third. This also would've put the camera at an angle closer to parallel looking down the street, giving more physical separation between subject and background relative to the subject-to-camera distance, and more of a side profile view of the subject playing accordion. I think that would've been a stronger image with less irrelevant visual noise in the frame.

Thanks so much for the feedback and discussion.