More Words, Deeper Hole

I don't know about sympathetic, and I don't know if it's still in effect, the Penguin realized he could make almost as much money legally (and keep it) by going legit, and so started a themed nightclub, with a little gray-market activity on the side. He had a deal going with Batman providing some info on what was going down from time to time made sure the Bat chose not not delve too deeply in some of Penguin's law-skirting activities.

The Riddler became a private investigator when he realized that all trying to outwit Batman with puzzles was doing was landing him repeatedly in Arkham, and there's more than one way to prove yourself intellectually superior than someone else, such as being better at what they do than they are. So he decided to demonstrate he could be a better detective than Batman, with the side-benefit that his puzzle obsession worked for him. IIRC, Batman even used him as an investigator on the odd occasion, which delighted Nygma to no end.