Thanks @ChefByzen, I enjoyed this machine a lot. Just right amount of CVE, guessing and enumeration.
Hints:
Foothold - check what is used and how old it is. Do it by hand if sploit fails.
User1 - search for interesting files, find interesting pattern. Maybe ask chef if he can help you.
User2 - check how can you login with that username. What would you use if you are User1?
Root - you are going places. Google if you are already famous?