I agree with Brian, in the sense that as a 'journeyman' tree man, one MUST be able to evaluate if a tree is going to hold your weight or not.
But I also agree with taking the time to really check it out.
If production is not an issue then why not have fun with it?
One the other hand, in my business I really have a hard time with some climber I am paying for dinking around and wasting time.
When I learned tree work, I learned from a guy who really didn't care that much. Dead tree? He would say 'just get up there and cut out your body weight, you'll be fine'.
Lucky to be alive today.