my kestrel experiences are from the Leslie Spit and Brickworks. so maybe there's the typical "east end" vs "west end" toronto personalities happening.
the Leslie Spit one sometimes doesn't care if joggers get close to it. but it will remain perfectly still.
the Brickworks/Don River kestrel(s) are the same or a little more timid.
the kestrel i saw at Sam Smith was strange. INCREDIBLY vocal. never heard a kestrel KIP-KIP-KIP! so loudly and for so long. i was "relatively" close for those shots (it was 10+ feet up and i was 10 feet from the tree, standing on the path). it did fly away but not that far and, again, was so vocal.
when i was shooting the goldeneye that was swimming by the docks, the kestrel flew to the top of the the first boat's mast and was keeping an eye on me. he stayed for a few minutes then flew south.
not alarmingly strange, but yeah, seemed to be kind of friendly and curious about people.