Been an IT for 13 years man.. yes trust your tools, especially fluke line testers, they make our life ten times easier and jobs faster. a couple other things i've learned over the years:
1. Always get the full story from the user, and hopefully they tell it to you, so you can actually diagnose the issue better, even if they don't want to tell you their embarrassing details about what they were doing or downloading during the outage.
2. It's almost always an update/reboot or physical issue.