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Owner goals should make sense for the owner's profit vs. winning relative preference.
The hometown player one (even though its implementation clearly has a bug) reasonably makes sense from a profit perspective. The owner would figure (and this should actually happen) that the hometown player will drive up interest in the team, making more money. A heavily winning-focused owner should never make that a goal.
Extending a given player should generally only be made a goal with highly popular players (again, for team interest). That may already be part of the calculation.
Dumping a distracting player I've seen, and unless it's a dump for salary rather than for "clubhouse distraction" reasons, that would be more a Winning owner type goal.
Improving a position really should always be a particularly weak position from a Winning-oriented owner. It shouldn't be given that often, while improving a given stat makes more sense, and should always be a deficient stat-- although I can imagine an owner who loves power or speed or pitching or whatever ordering a stat related to that to be improved; but then it should be consistent from year to year that the owner focuses on power hitters/speedy guys/hitters for average/OBP guys who work walks/pitching and defense/etc..
If I owned a low-walk team in real life I might order the GM to bring in more selective hitters, for example. But then I'd be consistent and not a couple of years later complain that batters weren't putting balls in play or something.
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