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This is a cool idea. I've been thinking about how we've got wiki art galleries of specific artists or ships and how cumbersome they are to make new ones. You've got to search around and will probably miss something. What if a ship has unified art from one artist but then moves to a new artist for later batches? It's hard to organize all of that and have them still viewable in the media manager, as you said.
For example, my plot the Kokatsu had a cool lineup of portraits at launch, but now only three of them are still aboard the ship. They're nice to look at as a set. The same could be said for any ship's roster that has had periods where everyone has art, like the Eucharis has in the past or the Kaiyo does now. Being able to see a gallery of "Star Army Admirals by helloimtea" or "Kaiyo II crew, YE 42 by tutti_fruppy" would be a boon for the RP and be able to showcase our history via the art commissioned by members and the site.