DC head canons whil tipsy, Batcats love language is Bruce buying her increasingly expensive things, art, jewelry, you name it, she wants it? He'll buy it.
Except he knows that half the thrill for her is the B & E. Without a little breaking and entering how is she supposed to feel like she earned it???
So Bruce of course creates the solution, and sets it up where she gets to steal it instead. They're are always elaborate security systems, things he knows will test her. Sometimes in the less traveled wing of Wayne Manor itself, a show of trust. Leading her back to his home and waiting to see if he'll wake up to a ping on his security system and a note where a beautiful diamond necklace was. Other times he'll take over entire wings of the Gotham museums and galleries. Tailored specifically to Silena's tastes so that she'll have the pick of the litter and he can either keep the rest or auction them off for charity.
He narrowly avoids insurance scams half the time by playing up the Brucie act. People are horrified that he's just been robbed blind, there are art enthusiasts all across the globe trying to walk him through the insurance claims while he's just trying to to wave it off. The art galleries and museums are setting up full scale meetings, insurance people included with PowerPoint presentations of every step to filing the insurance claim and Bruce is sweating in his armani trying to laugh off how much work it is, and really he'll get to it eventually (read never)
There's a 50/50 chance it winds up in his own manor eventually, he's not getting arrested for Insurance Fraud. It'll interrupt the batmanning