I have also been haunted by this small bird - it flies high above very quickly in the evening. Is it some kind of nighthawk?
I have listened to the songs of the sharp-skinned hawk, northern goshawk, lesser nighthawk, common nighthawk, common poorwill, eastern whip-poor-will online, and none is correct. I checked all nightjars that live in ontario that were listed on main birding sites.
It sings a haunting, almost loon-like woo woo woo woo and I think it is an evening hawk of some kind - not an owl.
If anyone can identify this bird I would be so grateful! It is ubiquitous, spring through fall in evenings in eastern ontario south of ottawa, fills the evening air with mournful, lonely calls.