Oof, I am getting a headache just imagining how much coding that would take! And, I doubt that the old fart system FeralHeart runs on would be able to support such a thing. It is a brilliant idea, so I will give you that. But, virtually impossible to do with the outdated system of Ogre.
If anything, FeralHeart could host art parties through join.me or Youtube livestream. Several artists can be watched through either program, taking requests or just drawing for the heck of it. Or a live art contest/Pictionary! It can take place in a art-themed map, hehe.