CC Illustrator - Saving Issues

I recently worked on 11 seperate illustrator files between 7-10:30PM, each containing seperate identity concepts. I periodically save while I work. I did not work on these 11 at the same time, but across the span of time. I may have had maybe 3 up at one time. Once completed, I would save...THEN save again as a PDF. I had to send these out so I did not preserve illustrator capabilities due to email size restrictions. Before closing any file window, I would just resave to be certain as an AI. My issue starts here...
I went back to the AI files to relook at something. Three of the illustrator files do not have any changes made to them. Time didn't seem to matter as two of the files were created and saved towards the beginning of the work span and the third was created and saved last. When I mean nothing is saved, none of my work - AT ALL! I now have a blank canvas in one document, and two other outdated documents, yet all the PDFs are fine in reflecting the point at which I finished. Is this currently a known issue? Does anyone know how I would go about correcting the failures to save regardless of manually saving? Even the time stamps reflect no changes even though I was actively working on them and saving constantly. I know I'm not crazy!

That seems like a really bad system. So people who don't have printers connected automatically start off with the possibility of more issues?
I created a new file and placed the empty file into it, it came up blank. I created a new file and dragged one of the other files that are outdated and it came up fine, but again outdated. I tried dragging a PDF into it also, and that came in fine. Only like I said before and you mentioned, it doesn't have AI Editibility so it only gives me an option to image trace (which don't come out so well).
I created new files on a different identity later on the evening after my initial issue. Those work perfectly.
Sorry missed your question: I have not updated my creative cloud. I had the version before the newest at the time of working on these files.

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    Opened
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    Product
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