Personally, I like this exercise of overanalyzing, but only because it's for a short, concentrated time. The mental effort we're putting forth can offer you long-lasting benefit.
Deep, mind-stretching consideration causes you to think more during your work day about what you're doing, and why. For me, how sharp the chain is, and how fast it cuts <b>directly affects my income</b>. As well, it affects how hard the saw works, how the bar wears, how much cutting gets done per tank of gas used and how much work gets done by the end of the day.
When you're cutting through wood, you should be entirely focussed and present in what you're doing. Every part of every second you are keenly aware of what is happening. This translates into how you <i>feel</i>. A sharp chain, slicing swiftly, cut after cut, is joy. A not-sharp chain requiring pressure, blowing fine dust or cutting a curve is not joy.
In the tree business, you ARE your tools. How finely tuned they are is an extension of your personal performance. Sharpness equals predictability equals control which equals safety. To truly pursue the outer limits of your technical abilities as an arborist, the sharpness of your chain is a critical element.