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.
It shows up for me.Have you waited until Day 2?
You need 75 Sluttiness and at least 1 energy to offer sex during the robbery.
You have to beg Jeff first. Once you've done that, sex should show up as an option.
All good.
