I can't seem to upload custom thumbnails.

This sounds like a browser issue. I'd recommend deleting cache, and cookies, closing the browser, starting it again, logging back in and trying again.
 
Well..
I just realized that Firefox just wasn't uploading it properly.
You were right, I should have uploaded it on Chrome.
But why doesn't it work on Firefox?
 
I sometimes have this issue on the first try, I just try again and it's fine. Usually if I try to do the thumbnail before the upload is at 2%, that's when I have trouble. I also make sure I don't make it any bigger than 1920x1080, and make sure it's a JPG and not a PNG, that seems to minimize problems. (Chrome user here)
 
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