its great that you put so much thought into something like this but the reality is, there are far too many variables from year to year to even try and predict what the Sox roster would look like even a year from now, let alone four.
the value of prospects fluctuates from year to year as do team's needs and spending ability (five years ago, Toronto couldn't spend s***). The market constantly fluctuates putting a premium on certain positions every year and then after all that, you gotta look at how unforseen circumstances change the course of action to make the Sox better. If, god forbid, Jason Varitek suffers a major injury next year and is relegated to backup duty, if that, for the rest of his career, prospects all of a sudden become trade chips in trying to fill that gap.