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I don't have definitive answers to either question, but I'll speculate FWIW:
1. This may have more to do with game design and programming complications than anything to do with realism. Unfortunately, a computer sim runs into blank walls sometimes. This may be one of those times.
2. The AI is clearly programmed to put a dollar value on players, and it probably does that pretty well most of the time -- that is, the AI won't overpay for someone. The programming that lies behind the AI's ability to evaluate a team's financials is ... rudimentary, shall we say. Your ability to make a holistic assessment of what's in the best interest of a team financially is going to be better than the AI's. The AI just spends money until it can't spend money any more.
My best guesses.
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