RE: How far is too far?
I've passed up a 190"+ (seriously)buck at 40 yards several years back. This year I passed up a beautiful 145-150" ten point (tons of mass) at 35-40 yards.
I think I stood a really good chance of getting them. I'm a close range hunter tho'. Iwould rather pass on the shot than feel like I'm shooting beyond my comfortable range.
IMHO, If you're feeling uncomfortable about the shot, then you probably shouldn't take it.