av8trflying, don't assume that just because a pilot has more experience or flys a bigger machine that their opinions or decisions are worth listening to either.
I have only come across of a small number of pilots whose opinion I respect and go to and ask them questions, particularly related to challenging weather. Only one of these was a chief pilot as well.
I think you question/ post was a good one and I hope you can find a mentor that you can go to with such good questions and come back with responses that help you make safe and professional decisions.