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Looks like a couple of things are going wrong there, for some reason it's applying a transfer window to signing a player contracted to your farm team when it shouldn't (I think there's a database setting causing that) and it's not allowing you to sign players from your junior team instantly. I'm not sure of the cause of the second one, so we're going to have to take a closer look there.
For now, if you want to get around it before we have it fixed, you can cheat a bit by starting a new game that's not in challenge mode turning commissioner mode on in it (the Manager Options screen), then exiting and saving, and copying the game_settings.dat file from it to this save, overwriting the one that's there. That'll allow you to edit a player or two onto your team so you can play that last game.
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