root@ready:~# id
uid=0(root) gid=0(root) groups=0(root)
root@ready:~#
Rooted! 
Overall a really frustrating box because I hit rabbit holes hard. Finally rooting after the “middle” hop took less than 5 minutes. 5-6 hours of wasted enumeration hurts… but oh well I guess you live and you learn.
Feel free to DM for nudges.