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One word of caution. Not every team always accurately understands which of those three phases they're currently in. A great real-life example of this is the Mets, who act like they're a Contending or Pennant Race team but in actuality should be in a rebuilding mode. Another similar example is the Diamondbacks.
A slightly different example might be the Giants, whom many people thought were in a rebuilding mode this winter, promoting young pitchers and letting some high-priced guys go, but their management was actually applying a Pennant Race strategy.
While the three categories you've got listed would seem to be an improvement, I think they might pigeon-hole teams too much. And teams should be capable of making mistakes recogizing what they should be doing, just like real MLB teams. I can see the complaints already: "This AI is broken. The White Sox are obviously a Contending team, but the computer is acting like they're rebuilding."
I think implementing this might open up a whole new can of worms, and needs to be thought through all the way.
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