Yes.

Oddly it works on my laptop just fine so something must be conflicting with it on the software side of my PC but I have no idea what considering I’ve used different browsers and cleared caches.

It just tries to add a picture with the same file name thus it takes the thumbnails from the last picture with that filename and applies those thumbnails to the newly uploaded picture for the new video. So you end up having the same picture for two different featured videos even though they’re completely unrelated. Sure, it still adds the featured video fine, but the thumbs are all wrong.