You'll need either 20+ Notoriety or the Thug Life tattoo during your initial meeting with the Old Man to unlock the option to break into his house.
Ok so that was the issue. I had forgotten that you can only do it on day 2. But how do you get more money from Jeff? Even though I stole all the cash I can only return it to Jeff if I hide. And flirting only gets me 50 bucks. The devlog said that if you took 500 and hide, you can choose to bribe Jeff to have sex with you. Is it a lust thing?