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The watch and the gun. If Ash can figure out how to manufacture shotgun shells in medieval times so can I. I'll also introduce the clock early and be praised for my genius
Shotgun ammo is really, really more basic than handgun ammo. The latter have higher tolerance requirements, the ammo requires fine machining and metallurgy not available in medieval times. Even reloading, you only get so many reloads out of a case before stresses start to cause failures in the casing. And ammo failures in handgun ammo can have catastrophic consequences.
Whereas a shotgun is a fancy musket. Shells are comparatively simple, and the requirements for the casing are a simple base that could be made by a competent brass-smith and some stiffened, waxed cotton.
In both cases, you're going to be fucked finding or making primers. While you could eventually work out making black powder - again, sufficient for a shotgun but in no way workable in any modern pistol - primer explosive needs more complex chemistry than you'll be able to work out. Primers and their placement are precision components.
You would be far better ignoring the handgun and bullets, and just build blunderbusses and canon. Those just need a good blacksmith and figuring out how to make black powder.
Exactly, also, anyone taking the gun and the bullets has obviously never used a handgun. Your chances of doing any damage is pretty low without a ton of range time, which takes bullets. Hand guns aren't accurate at any kind of range so you'd make some loud noises and that's about it. If you did manage to actually hit anyone, an Archer would kill you from way beyond your effective range and just take the gun and any remaining bullets.
The gun is the absolutely least useful thing on that list after the bullets.