Ha, thanks! Yes, there's a crunch. Jack's bills stack up on a timer, and the bottom one comes due first. You can go into the red once, but if another bill lands while you're still negative, the house is gone.
The town jobs are how Infini pays those bills, so fixing up the town and keeping the house aren't a choice. They're the same fight. What you build on the rig and how you handle the house decide which of the 12 endings you land on: six keep the house, six lose it.