Why is my Asset showing a different orientation than what was uploaded (displaying as vertical orientation instead of horizontal or vice versa)?

If you rotate the orientation of a pdf in Acrobat, you are only rotating the view. This setting is not retained when you upload your PDF into Pressero. This is an Acrobat behavior, not unique to Pressero. You need to rotate the file in the page layout program you are using before saving it as a PDF.