Finally rooted this badboi, what a journey!
User 1
Think of a technique that involves trying one thing against many other things, like spraying if you will. Enumerate to find the thing.
User 2
Search for interesting text in files.
Root/Admin
More than half the battle with enumerating this box was knowing which path to follow, because nothing jumped out (maybe a sign of my inexperience). Annoyingly none of the enum tools like winPEAS, PowerUp, etc flag the key info as being something important. Bear this in mind! Luckily some of the hints on here helped nudge me towards the right path.
With the exploit, don’t attempt to copy the file to local unless evasion is your bag; Something will get in your way. Also, the executable needs moar bits!