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This is an interesting topic to me and I will be looking more closely at my fictional league today with an eye towards this sort of thing.
My initial feeling is that I do see players on the AI managed teams in my league transition as they age from more challenging positions to less challenging ones in ways that seem to mirror real life quite well. (Thinking about center fielders who have transitioned to corner outfield positions and third baseman who have transitioned to first base and corner outfielders who have transitioned to first base. There is no DH in my league.) But certainly I've also seen players stay at their original position far longer than I would have kept them there, beyond a time when they had defensive value at those positions. I'll look more closely at my league, as I said, to see what the balance between these approaches looks like.
I would say though that I think it would be wrong if the AI always made the logical decision on these matters, if players always transitioned positions based upon logic alone. Because, in my experience, players are kept at positions in real life that they probably shouldn't logically be playing all the time. Sometimes this is because the team just doesn't see any great alternatives, sometimes it is just the entropy that sets in with the way a team sees an aging star player. ("Okay, the metrics guys tell us his defensive stats have declined, but he still looks pretty good to us, there is probably something wrong with the numbers, and hey, he won a Gold Glove out there 6 years ago, he can't be that bad, right. Besides, you want to be the one to tell him he's not a center fielder anymore?") As a Rockies fan, the example I immediately think of is how much longer Charlie Blackmon stayed in center field than he probably should have.
So while it is always good for the AI to be improved to make better decisions, I would never want it to make such logical, flawless decisions that it no longer actually was any good at all at mirroring how real life human decisions are made, how often they are not logical, how often they are flawed.
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