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If you go to the dialog where you link to the popup you will notice that the Link To button is disabled as soon as you select a popup, auto sizing or custom size. That is because for whatever reason, popups are not intended to be used in that way.
I know that you can select in the way you did and then change from Display in Frame to popup and the target will still show but the Link To dropdown is disabled and therefore the content is ignored.
If you create a topic with just the image in it, then you can link to that as a popup. Like it or not, that appears to be the way it was designed.
Images are included in the output but only if the link is created in a way intended by the designers.
I've found a method for RH to get you halfway there.
You can import an image as a baggage file and find it in the hyperlink dialog (link to file, navigate to the imported image). This is a lot faster than
1. Creating a new topic (name, properties, etc.)
2. Deleting the boilerplate
3. Inserting an image.
Still, RH won't self-size or let you self-size the popup window.
So you're trading one chore for another.
A couple of benefits, if you consider them so:
An image in a popup window will shrink and expand (up to original size) when you resize the window. You can't resize an image in a topic popup.
If you are (or anyone else is) interested in trying this, please reply here and I'll post some suggested code.