As said here what a fun and challenging box!
User - Enumeration is key. Look at what you can do on the open ports. Here may lie some interesting files.
Root - Again enumeration is key, maybe use some of the same methods as user (with some slight c…
Initial Foothold : Fuzzing needed (consider syntax if using dirb or similar).
User: Python code reading will be needed, take your time to understand what's happening.
Root: Easy enough, quick enum should show you the way.
Big thanks to @D…