I'm sorry to hear about the numbering list issue you're seeing. I'm not sure which version of Jive you're on, but when I create a list, I've always used Shift+Return (Enter) before inserting an image and then a normal carriage return at the end of the image to resume the number. I delete any excess lines when they're present to restart/adjust the numbering. For example, here's your same data (using copy and paste without formatting) being edited in the Jive Community:
And here's an example from scratch:
After the image, are you doing a carriage return? And are you creating the list from scratch, or are you editing existing data (first screencap)?