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One way to answer this question is this: if the AI is managing your minors, it will release a bunch of players to get the numbers down. That's pretty realistic, but what happens is suddenly the free agency list is much longer, and over the course of many seasons, it can get pretty long. There are work-arounds for this (basically trimming the free agency list yourself every season) but they are cumbersome and some people have complained about it. Don't know if this is likely to be fixed in OOTP10, but it might be.
If you are managing your minors, then of course you can keep everyone around, but it's not very realistic and can get pretty cumbersome too.
Hope that helps.
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