Dale so of course I'm already dead.
Basically if you make logical, cautious and compassionate choices you will be Dale every time.
On an hypothetical exploratory mission like what they posed you don't want attract attention so if you can avoid being seen by walkers and avoid shooting them then do it. If a guy has the drop on you with a rifle you definitely don't go for your gun. If he hasn't already pulled the trigger then the logical thing is to try to reassure him that you mean him no harm. The hardest choice was the last question. If the women is beyond help, then you definitely don't waste any medicine so either put her out of her misery or get her away from the group and comfort her; either way have your gun ready.