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I've umped on a few fields that are very similar to what I'm imagining with your description. What we usually do is make an imaginary line from the last dugout post to a post of the out of play fence. Depending on the fence, it may be 1 or 2 posts from the end. The method we use for deciding is that it must be a post that, if the ball is right there, a fielder can throw home with no obstacles (ie. dugout). If the ball goes in that area, dead ball; Period, bases awarded same as any other dead ball. Hope this helps.
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