Well, things are still going OK and I'm pretty happy with my progress. At this rate I'm rooting at least one box a night after work.

I've definitely sped up and improved my enumeration skills, which is helping me with the initial entry point into the target server. As like everyone says, enumeration is king... and it really is. Spending that time reviewing and looking through everything your nmap, nikto, dirbuster etc scans present is a good way to make sure you're not missing anything. 

I've also come to learn about testing the basics and trying stupid things that seem obvious, where you would think "nah no way"...  but it work!

Today I just finished PAIN!

I got my initial limited shell quite easily, comped to other servers. And I thought really? Is that it? Then the real PAIN came with privilege escalation. 

Again, like my statements above. Take a step back, enumerate again once you're on the system, think, READ any exploits you've found. And just think about it before running it. What's it trying to do, what does the target system look like etc..

A bit of trial and error, I got it working and saw that lovely shell appear:

#uid=0(root) gid=0(root) groups=0(root)

BOOOOOOOOOOOOOM!

--> n33dle