I must be getting to be an old pharte, I guess.
I am concerned with
(a) not killing myself or those along for the ride with me
(b) having a plausible story for the inquiry if it should turn to custard along the way. Having had the opportunity of observing the legal process, their views of what is reasonable might just not be congruent with mine so a pinch of conservatism always looks to be attractive.
safetypee's professional credentials for this discussion are far more than most appropriate.
As for me, depart in a significantly gusting tailwind ? Engine handling problems, possible pitching moment problems, distance problems, low level wind velocity profile problems ? No thanks, not unless it is a case of in extremis and the bad guys are shooting big projectiles or something of similarly dire eyebrow-raising status. As a mentor many years ago offered when I made some stupid, commercially driven suggestion as a newly-minted F/O ... "not even worth our time thinking about, young John".