Upload wit Assets means you upload the source PPT(X) file and the folder with the Presenter source folder.
For the video in quesiton, was it inserted using the Insert Video function int PPT or Presenter?
I added a video as an attachment like a handout. It did show up in the paperclip area.
I didn't know if it was needed for a video that I had inserted via the Presenter tools. Apparently that video went with the presentation without doing anything extra. I assume that videos that are inserted via PowerPoint tools cause a problem correct?
As an attachment, it should be available through the paperclip button throughout the entire presentation. This video won't play back as part of the presentation but can be downloaded and played locally on the viewers computer.
If you want the video play back in the presentation, you will need to insert it through the Insert Video option in the Presenter ribbon.