I've done it a few times. I try to set up a challenge like living only on Timberwolf and getting all the achievements, or never using the rifle (which nets you at least one achievement). I'll probably try it at Forlorn when when the next update comes. I'm trying to finish my Timberwolf run before then, only need to catch a big fish, kill another bear and make a bedroll, and 200 days (I'm at 149 I think). When I get better at Interloper I'll probably reset and give that a go too.
I can kill 20 wolves and still get that achievement. Only if you actually kill them in a fight does it block the achievement. If the wolf bleeds to death from damage sustained during a struggle you still get the achievement. I've gotten this achievement at least a dozen times (I like to reset my achievements and see if I can get them all in a single play through). Your journal will say you killed a Wolf, but it doesn't count unless you deal the deadly blow.
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