I can’t explain how frustrating it is to spend hours on a box just to realized that you missed something small. This was a huge problem for me starting out, but as I got more experience it became a lot easier. I wrote a basic external enumeration and recon guide for people new to HTB. Hope it gives you at least a starting point.
Run nikto against sites - its always worth a background scan while you do other things as it may find some oddities and can return directories faster than dirb/gobuster/dirbuster etc.
Check SSL/TLS certs - the details may give clues about usernames or subdomains.
Depending on the level of detail, if a DB server comes up in the NMAP scan its worth digging in deeped.