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Yeah, the big stack's position is what has me worried in these types of situations. If the other small stack is directly to my left it makes life a lot better.

I think I'll add another layer to the question: which is the overiding factor in these situations, your chipstack relative to the next smallest stack or your stack relative to the blinds? I definitely push with a narrower range when the stacks are closer and I'm wondering whether or not it's a leak.

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Nice question. If the other short stack has so few big blinds left that he is forced all-in very soon, while you are not, you should only push good hands (unless he is directly to your left, but that's not the case here).
If you have more chips than the other short stack, but he also has more than, say, 4 big blinds, don't wait. He could stay alive for a few more orbits and if he doubles up you're screwed.

The call ranges of all players in this situation are very important. If they all have a small call range (they are tight) you can still push many hands.