Yes, you can do that if you use the old wiki markup:
Create one page where you attach all the images and then include the images on all other pages with
Just start typing and it automatically shows a drop down menu with the images available in that space.
If you want to include an image from another space you must also add the space name and use:
I'm not sure if this is going to work but have you thought about the excerpt macro?
You could have the image in the excerpt, display it on multiple places and you'd just have to update the picture once...
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