[@ProPro]
Be fair, those riddles were few and far between [i]and[/i] were ones that related in some way to Dick's interests. Like the one in Gotham Adventures about jazz.

I think it's really about how the relationship between Nigma and the bat family develops. With Bruce, it was about proving himself Batman's intellectual superior. But with Batman gone? As much as I love Dick (hehehehehehehehehhehehehehehehhe), he's not Nigma's intellectual equal.

I'm thinking that he should leave clues that mislead them and send them to the wrong place before finally, after a grand crime spree, be brought down by his own arrogance in some way.