I do the rule of 3's thing as well. I entertain my gut feelings and try to figure out what it is. Some days the universe decides to kick my butt. I sometimes dare it to kick harder out of frustration and it obliges me, to which I respond "I was being sarcastic!"
The drone job adds a new level of CRM for me. When your butt is on the ground safe and sound, it is harder to maintain that same mindset. I am 2.5 hours from home right now waiting on an appointment when winds are forecast to gust in the high 20s. If I don't do this job today, I will have to fly it later. The homeowner and contractor who will be there want it done now. My company wants to show that we can handle the influx of appointments and be flexible. I feel like I have to justify my paycheck with results to my employer as well as make the 5 hour round trip worth it to the company.
My life isn't in danger but I still have to have good ADM. I will probably end up cancelling this one based on winds in front of the contractor and homeowner which also puts pressure on me (come on man I need this done my home is leaking/i want to get this guys roof fixed so I can get paid/we don't want to wait for a reschedule/etc).
Knowing aircraft limitations is also pretty important. I am not sitting in the aircraft so the seat of the pants feel isn't there. The drone can handle 30mph+ with GPS hold but if you suddenly lose it, can you react fast enough to keep it under control? If winds are that high and you are right on the roof there are turbulent air pockets everywhere that pull you different ways which is hard to react to unless you are in the thing. Definitely a new kind of challenge.