If you do not enable injuries, you should have no problem. The transactions file determines when a player is placed on the IL and when they are activated from it again. Disregard the "255 days." It means nothing, other than keeping a player out of action until the transaction file indicates he was activated in real life. If you notice a player never returns from the IL, just note the player's name and the season. We can then check the master file for any errors.
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