If you use Multilinear Plasticity, you must convert from Engineering Stress to True Stress. You said you did not. Please show the material model you are using.
I wanted to see how close the hole is to an edge of the part.
If the hole is less than one diameter from an edge of the part, then that edge and the adjacent hole wall can deform outward in a way that the hole wall 90 degrees around cannot. That would make it so you can't use symmetry and the problem would be extremely difficult to simulate. I'm going to assume that this is not the case since you would need a massive cluster of computer cores solving for a week to do the entire pin in a hole near the edge.
If the hole is more than three diameters away from an edge, then the pin entering the hole will behave the same as if the hole were in an infinitely large part. In that case, you can use symmetry to slice one row (or two rows) of teeth because any row (or two rows) is the same as any other row.
So let's consider the symmetric case. Viewed from the hole, there are 44 identical teeth around the circumference of the pin, but every other row has a half pitch lag. Viewed from the side of the pin, a row has a first tooth, then the rest of the teeth in that row. The first tooth will act like a tool and gouge a groove into the plastic. The second, third and all the rest of the teeth will follow in this groove. The groove may spring back slightly after the first tooth passes, so the second tooth will have to push it back out slightly, but not the way the first tooth had to. That is why I recommended a one tooth model. On second thought, a two tooth model would be better.
I recommend you get a small model that solves and teaches you something about your problem. That is much more useful that a big model that will not solve and teaches you nothing about your problem.