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Machete, Water Purifier (provided it does not need electricity to work), German Shepherd and the tent. If the water purifier requires electricity, I'd opt for the body armor.
Stuff that requires fuel, electricity or ammo will become obsolete after a certain amount of time, so the flashlight, crossbow, motorcycle, chainsaw etc. only have limited use and become dead weight eventually. The first aid kit might help with "regular" injuries, but is likely useless against zombie bites getting infected with whatever virus is responsible for their mutation. The respirator mask is only useful if there's something dangerous in the air, and will only stay useful until the filter gets too dirty / too old and needs to be replaced.
The reality is that every item is finite if you can't maintain it. Some are naturally longer lived than others (machete, fireaxe) but require sharpening and will eventually break. The better metric is what kind of utility it provides during its life, with a second metric for how easy it is to maintain. Something like the Jeep may only get you a week of functional time, but it's going to allow you to set up so much easier.