The random sexual encounter at night with Alan will give you the option to split the money (best option to avoid cops and you will raise also INT!). You need to be neutral to have it started and will raise attitude, is closed if you've sub or slave attitude.
Once your crime is enough high you will have also unlocked the option to advice the thug in the morning about cops when he rob the old lady! (this will always works also in case of sub/slave/neutral attitude, but as said you will need atleast 20 crime point to unlock it if i recall good)
In Prison Razor will give you pills, he will get those back on the day of the release and you will have money in exchange, should be around 50 each..