I've just discovered this thread and have spent the last three days (off and on) reading through the whole thing.
I have to say a big thank you to all who have posted pics and links. It has been fascinating to look back.
Waaaaay back in the thread someone had asked about what looked to be a drive-in theatre on Henderson Highway where the Sobeys is now located. I can tell you that there was indeed a drive-in at that site, I believe it was called the El Dorado. I discovered this while reading through some of the articles on this site:
http://www.mmcalumni.ca/v2/history.php?p=ek
I haven't even come close to getting through all of the articles, but this is a great resource for tracking the development of this area of Winnipeg.