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I like the stories that have Riddler leaving his life of crime to run the world's most difficult escape room. I like that the modern era offers him such a unique business opportunity that could help him with his mental health and villainous impulses.
But I also fucking CRAVE to see a story where Riddler gets super into the DC version of Dungeons and Dragons and becomes super famous for his Dungeon Master skills. I think that having people's beloved characters in danger would give him an even better thrill. I think he'd love to devote his time to learning backstories and lore so he can personalize dungeon riddles and enemies.
Tim would be the one to suggest this to him, I bet. Sends Eddie a text about needing a riddle suitable for his own W&W campaign but not having the time to put it together himself. I bet Ed would fall into a rabbit hole of research and wind up with so much KNOWLEDGE that Tim's like, "Hey, maybe you should put together your own campaign book and sell it online"; thus, the Riddler's Run becomes a legend for players.