Any trained monkey can administer a system that is working correctly. Such systems rarely, if ever, need external human, or simian, guidance. The system gets some sort of stimulus or input, makes decisions, takes actions, and most likely emits some sort of product or information. Easy enough. Watch the big wheels go round.
Good system and network administrators earn their salaries when systems are not working correctly. It is when nothing seems to work correctly, debugging data are scarce and managerial or client pressure is the highest that time spent preparing for disaster pays off tenfold.
Using the FreeBSD ports collection is generally an exercise in knowing what command to type and when. Again, trained monkey work. The secret to using the ports collection well is knowing what to do when the output of the ports collection isn't exactly what you expected.