rooted! 
The initial foothold is always a hassle for me, especially on the free plan.
Switching to US servers improved the experience a little.
Initial Foothold: scanning for the right extensions and a custom wordlist did the trick, but I’ve been required to modify a py script, the same way I did on a previous HTB machine.
User: it’s all about enumeration. Once you’re in, just look for credentials and you’ll soon be someone else 
Root: it has been super easy and a little unexpected. Even if I’m not following CVE updates so often, a quick search on google has taken less than 5 minutes
Thanks @egotisticalSW! 
P.S.: so, I suppose those pictures were intended to be there…