You were not kidding about the signals being confusing. Why are they on the wrong side of the road? And why are there "no pedestrians allowed" signs right next to what looks like a sidewalk?

I could understand having no-bikes signs at Allen @ Sheppard if Allen transformed inevitably into an expressway without the possibility of a detour, but there is indeed a detour at Transit Rd to avoid entering the expressway. So why would bikes not be allowed? To be clear, riding along Allen Rd looks pretty suicidal to me, but OSM doesn't seem to recognize suicidal=yes tags.

Just for fun I tried this on Google Maps in cycling mode and it allows traveling south from Allen Rd @ Sheppard... until Allen Rd widens to four lanes, at which point it just refuses as if the road had ended.

Please let me know if you get any info from 311. Right now it seems to me like OSM is correct as-is.