I have figured out a workaround for this, it's no fun but it does work
The glitch seems to be that it takes 4 tries, and do not bother uploading an image to anything aside your own image gallery.
First try you will likely load up to 10%
Second try you may load 100% but the image will not show up
Third try (leave your image gallery and then come back) you will load 0%
Fourth try you will finally upload the image.
Annoying yes, but if you really want to upload an image it does work, you can then proceed to add it to the page you want VIA my images.
There is seemingly no 'perfect' way to truly say goodbye. So I gathered a bunch of them!