Hints for this box:
User - The name of the box and other various hints strewn around should give you general idea. This part is pretty CTFish. As alluded to in earlier comments, there’s a hint which will save you some time on one of the other ports.
Root - Congrats, you’ve survived more of the joy of CTF boxes. Start over and enumerate what’s on the box. With the additional access you have at this point, are things you may have considered before possible now? This part is much more like what most of us are here for, get back to basics.