I've been working with several teachers with iObservations this year to make sure their artifacts are uploading properly and are able to be seen. However, I had a teacher come to me today who, despite having uploaded her videos, was not able to play them some time after they had been uploaded. It is hard to tell where the catch was, but my hunch is that iObservations is not a fan of large attachments. So, the workaround is to include a link in the action step comments that will take the viewer to a folder on your Google Drive. Here is a screencast to walk you through the simple process.
If you need more help to get it set up, just let me know by making an appointment with me during my office hours.