Some tips for this box:
User - enumerate, find exploitable app. don’t let warning messages deter you - check if it’s open source and see what’s going on behind the scenes. be sure to be thorough and double check what/where you’re pointing things, adjust any tools or scripts you find to help with debugging.
Root - guaranteed you’re doing TOO much enumeration, think of one of the most basic things you’d check when popping a shell and google to check status.