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We all know that the period between these two tests represents a considerable adavantage for those having taken the test during the former time.

In your opinion, what kind of score increase would one need to have to bring the chances of acceptance back to equal, if the score doesn't drastically to either end of a spectrum? In other words, if one scores a 168 in October, what score would the same person need to score in December to give him/herself the same kinds of odds for acceptance at x school considering that many applications have already been reviewed? Does it matter at all?

Doesn't matter too much.

Both Oct and Dec test takers are already behind applicants who took the test in June and sent in their stuff weeks ago.

In my opinion, it won't matter if you take it in December. If you improve your score by even a point, you're going to jump more applicants with your index than you would by being in 2 months earlier.