You just need to spend a night at home with rank below 2, and dangerous work for money will be introduced.
Yay finally understood why the prompt didn't appear, i initially found way too much money, and kept rank 2 up for long, and had just 1 strike. Didn't realise you the game expanded after strike 2.
I also was going to mention what i noticed but i've seen the latest update. I'll follow the game for sure. Havent said it yet but the pixel art is soo nice. Great style!