I wish both parties would post "bounties" for tools they need that they don't have time to build. Much of it is built in the air for a highly specific context or bought off the shelf these days but there are some ongoing unsolved engineering needs.
Off the top of my head: I don't think there's a good solution to verify ad-buys in small markets. You could make a pretty penny sticking a webcam in front of an over-the-air broadcast TV in every county in every swing state and hiring someone to tick a box every time a candidate's ad plays.