I count seven. Are there more?
  1. Rap patrol on the gat patrol
  2. Foes that want to ensure Jay Z's closed-casket funeral
  3. Rap critics that say he's "money/cash/hos "
  4. Radio stations that won't play his hits if he won't appear on their shows
  5. Rap magazines that want to exploit him in order to earn more advertising revenue
  6. A harrowing incident of racial profiling
  7. Needing to strong arm a ho
  8. After aforementioned strong-arm incident, his bail was an inordinately high half a mil, because of aforementioned racial profiling
    Suggested by @chloesearcy
  9. Hasn't passed the Bar
    I think he mentions at one point that he hasn't passed the bar. I don't know if he ever took the bar or went to law school, but that is a real problem if he has any hope of becoming a practicing attorney
    Suggested by @mlh
  10. Paparazzi
    Suggested by @samantharonson
  11. Feeling bad for you, son
    His big heart gets him into emotionally painful territory.
    Suggested by @evanp
  12. K-9 unit
    Suggested by @samantharonson
  13. Addict cell mates going through withdrawal.
    Suggested by @samantharonson
  14. Holes in his zapatos (this problem has been solved tho)
    Suggested by @chloesearcy
  15. The SYSTEM
    Suggested by @samantharonson
  16. Tautological though it may be, having so many problems counts as a problem in and of itself.
    Suggested by @LevNovak