I'd always opt for the bolt. The 100s had a decent rep for accuracy, but they're old semi-autos. Bit harder to tell if you're going to get a good one or not. For hunting, there's not really any advantages of a semi-automatic rifle. If you want a classic, stylish semi-auto, then the win 100 is a good way to go. There's no guarantees you're going to get a tack driver. I would guess not, in comparison to a modern bolt gun.
My opinion: the safe choice for an accurate rifle would be a new bolt action. You can keep the price down via Stevens 200 or Savage 111.
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