1. It is working normally.
2. The first link looks like a link to the Gallery page that hosts the image. The second is the direct link to where the image is stored. (The image is stored on a third party cloud service (Amazon Web Services)). Either link should work. First one gives you the formatted gallery link.
Second gives you the image directly. (I shrunk it for this post)
Which link you'd like to use depends on your purpose of posting.
3. I think it is a security setting with your iPad. either VPN, or something about third-party or cross-site image loading.
Sometimes the issue is on our end where something gets cached incorrectly, but that typically clears in a few hours. This is pretty rare on a post. I usually see it garbling up a blog header image.
If someone has an iPad, can you weigh in? I think we had a case recently that was similar.