A bit like what the extension for A Learnable Meta already does: an ability to link images hosted offsite and have them show up in the trivia boxes GeoGuessr currently has.
The application I have in mind is a map I've been adding locations to that comprises album cover locations, and I can't help but feel that many locations aren't particularly interesting without seeing them in the context of the cover, especially for more obscure releases beyond the ubiquitous Abbey Road spots that everybody has already seen. 704 W. High Street in Urbana, Illinois, for instance, will just be an ordinary house for most people, but if people are able to see the American Football cover in the trivia box from which it came, they'll be able to appreciate the spot more (and consequently the map).