Thats what the shopkeeper option (easy prisons) is for!
the shopkeeper option on easy mode could be a little more forgiving. the shopkeeper option should be a lot cheaper to purchase getting the restraints removed, not upping the price 1000 every time you want to proceed with using her. it should be relevant to the amount of money you can pick up as a prisoner. or you could have the shopkeeper make a deal to remove the restraints, but add more of her own advertisement restraints so if you use her too much you would soft lock yourself into being her own walking advertisement.