How should Lightroom Classic handle incoming files of the same name from Lightroom Cloud

I finally figured out what appears to be an issue occurring over the last few months with images having capture date changed.

When looking at the EXIF data, there is the "date" and the "capture date" and many photos would have these be different after syncing. 

Here is an example: 

Without going through all the details, ultimately, I discovered that I had multiple pairs of photos with the same filename coming into the same month.

My workflow for phone photos is Phone -> LR Mobile/cloud -> LR Classic (PC storage)

My wife and I both sync our photos to the same catalog, so apparently, our photo names from our iPhones were repeating within the same month (generally this has not happened, but if you take enough photos, you are bound to repeat and eventually overlap). I discovered that two photos of the same name were in the same month in lightroom cloud, with one of them displaying the correct date (most recent photo) and the older photo being assigned the EXACT same date and time, which is, of course incorrect.

I then discovered that I only had one photo of that name on my PC, meaning it did not download both. I believe this is because I have my photos organized by year/month, and PC would not like two photos with the same file name in one folder. I switched to Year/Month/Day and it seems to be downloading both now (though I need to go and revert capture date for those photos in conflict.)

My question: Is this expected behavior or should lightroom classic be able to account for photos with the same filename when Lightroom clearly is able to differentiate?