Yes it does. If they go for any other weapon other than the pistol they get shot up and die. Because unless it's the pistol, he gets out drawn. That's just making up Character which doesn't flat out exist. Considering the pistol could very easily be in their bag, as well, most likely it is in their bag considering how many other weapons they have. Like you said. They only have a few slots. But they have Over A Dozen weapons. Over a dozen weapons could be taking up those slots. There is no reason he might not even have a gun in his slots. And thus would need to go to his bag and get out his gun which would cause him to die. The only win he has is if Out of all of the over Dozens of weapons the pistol is in his slot, and he manages to outdraw someone vastly more experienced than he is. Which that win condition is so unlikey
Which there is a huge problem. If the weapon is in his bag. He is screwed. He gets shot up to death before he can draw it. And with So Many Freaking weapons, and only 3 slots. Th odds of him even having the pistol is Extremely unlikely. And the odds of him having a gun even is unlikely. At the time, he could have range options, but all his range options are too short cause he doesn't have a gun in his slots. It's in his bag. So to win he needs this specifically
Out of the Dozens of weapons he has, and only 3 slots. He has the pistol in the slots and not the dozens of other weapons and or food.
He still needs to manage to actually fight with Gumshoe and not get shot to death by the much more experienced and trained fighter
That's his one win condition. And it's So Extremely Unlikely as it requires several things to go right. Cause if one thing is off. He dies. And that somehow happening 6\10 times is just not plausible to the slightest
And no. Not at all. That's not how a gun works. One bullet to the head would put The Player Down. Pierce damages gives Jack about him being that much more durable. He gets shot, bleeds to death get shot somewhere fatal, and dies. A gun doesn't care at all. Plus Gumshoe upscales from that. He is notably stronger than that feat.