RE: How do you decide when to .......
 

It all depends on the deer and the angles and distance and thier mood that they present to me. I've taken as close as 10 yards and as far away as 37.25395555567879 yards. :) Some just will not present me with what I'm looking for and those have walked.

It's mostly the angle I am concerend with and the mood of the deer, and since I never trim any shooting lanes they also have to come to a place that is clear enough to get an arrow through unobstructed..

RE: How do you decide when to .......
 

Good question. I know my shooting skills both on the range and out in the woods within any given yardage. For hunting I have set the limit at 30 yards and not beyond it. I know I can confidently place the area where it needs to go (within a small margin of error) out to that distance. Ofcourse, most of my shots are much shorter...under 15 yards actually but I know I can accurately shoot farther if needed.