Finally got root.
Hints:
User:
enumerate, enumerate, enumerate
crack what you enumerate
enumerate some more
Look beyond what you think is normal
play with the rubies
Root:
Think a little forensically
Grep and Strings are your friend
Don’t we always harp on credential re-use?
Feel free to DM me for hints.
Thanks to @minatoTW for making the box and @marlasthemage for all your help!