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Are you playing real transactions with minor leagues setup? I didn't know that the game even let you do that. When I play historical with real transactions, it disables minor leagues.
When a player misses a season, it just disables him for the year and places him on your team's IR. If there is a transaction that releases him, it does that, and he goes to the FA pool. He'll then be picked up again by whomever did so based on a future transaction. He may retire if he never shows up in the league again. It works fairly smoothly. There were a few bugs involved in these kinds of transactions, but they've been fixed with the newer versions of the game.
The only bug I'm still seeing is that rookies enter the game one year older than Baseball Reference says they should be. For instance, Ty Cobb entered a recent league in 1905 for me, and the game had him as 19. Baseball Ref has him being 18 that year. This has been a bug for a couple of versions now.
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