This is not meant as a detailed walk-through, more of a reference guide of useful commands and tips. This is meant for me but hopefully you too will get something from it. If so let me know - thanks!
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Check out Pentest.ws a tool I rely on so much to help speed up my workflow when attacking HTB or OSCP machines.
Thanks to guif, g0tmi1k, fuzzysecurity, practical hacking, xapax and all other sites I've used to allow me to collate this document.
No doubt there will be mistakes in this guide. Please let me know so I can improve it. Also if can you provide useful context on some commands like hints and tips - let me know so I can add them. Comment on http://offsecnewbie.com/2018/12/05/pentesting-guide/ to get in contact.