I enjoyed parts of this - other parts were intensely frustrating - all because of my inexperience - but I learned a huge amount - mostly through the help of @darkkilla - who very patiently guided me through the blocks I hit.
User: already said on the discussion but Python seems more reliable than Node for the first step. Look to the heavens and john to get the flag.
Root: take the easy path with the binary rather than the longer, well trodden path you took with user. Searching for the root flag - enumerate - or hit me up so I can do my penance for the help I got with this step.