I'm still not quite sure exactly
what you want to do, Fred, so excuse me if I miss the point. But if I think about adding street maps to localities then it might be feasible to work from the "other end", i.e. from the place-records, visible in the Records Window.
If I go to that Place Records tab and filter on a place name of Manchester, it brings up my list of localities in Manchester (because I've used a 4 part name, e.g. "Hulme, Manchester, Lancashire, England".) I could then add a map image to this place (in my case, I'll drag the image onto the Media tab of the Place property box). This will ensure that
any narrative report that uses "Hulme, Manchester, Lancashire, England" as a place-name will show that map image in the "appropriate" position.
The issue with that method is that, out of the box, FH doesn't make it easy to see whether any media have been attached to a place record. That
can be solved by adding a column to the Place Records tab that shows the count of media items attached to each place record. To do this, right-click the bar with the headings for the columns in the Place Records tab and choose "Configure columns..." In the resulting window, you use the left-hand side to choose what you want to show - in this case, you need to select "<Other....>" right down at the bottom.
Having selected it, click the ">" button to move it over and you'll get a dialog box "Add Column". This is what I entered into that box:

- Annotation 2020-09-08 132005.jpg (67.21 KiB) Viewed 10746 times
Click "OK" after, of course. The Media Count will show how many media items you've attached to that place so you can check to see if you've attached the map image or not. Except that's tricky if you add both a map and a town centre image (say) - it won't tell you which if the count is only one - you'd have to open up the Place property box and look at the media tab.
Doing it from this end, if you put a map against each place-name (using filtering to identify your target places), then you know that any report using that
exact place-name
will show the map.
Now, I said I'm not sure exactly what you want to do and this method will only work with place-names (i.e. in the Place Records tab). It won't work with addresses because they don't have an independent existence. And it won't work if you want specific maps shown against specific events. Nor does it give immediate access to the image from the events.
But if this method of adding media to the place would suffice then it cuts down the workload since you only need to work with each place, not each person or each event. Maybe?