For example this was my situation. I scheduled a fight with Conor Cooper. I scheduled it 6 months in advance and did 3 training days. Immediatly after finishing the training I accepted the challenge from Joe Frazier. I fought Joe, lost and continued simulating into the next fight. Only trouble was that my fight with Conor Cooper was scheduled inside of the recovery period after my fight with Frazier. At this point the game won't let you sim any days and won't let you sim the fight. I haven't retired my boxer yet but I don't see any choice.
I had something very similar happen on my 360. I scheduled a fight and then got challenged by the guy that was the champ via an email. I knew that the dates that the champ had available were too close to allow recovery from the fight I scheduled originally, but I thought that by accepting the challenge it would cancel my previously scheduled fight..the logic being that they have guys bail out of fights on you in legacy without giving a reason. Or if not, I figured the game would pick up on it and either not let me schedule the challenge or ask me to do it on a later date.
Anyways, the championship fight went on my schedule and it happened to be exactly two weeks after my previously scheduled fight. This caused me to have a training session and a fight scheduled on the exact same day since my first scheduled fight was exactly two weeks before the fight I accepted the challenge on. What happens is the game won't let you go beyond the training. After you either complete the training or auto-complete the training the calendar stays on that day since it sees you have a fight. I didn't test it a bunch of times, but this theoretically could let you really boost up your stats because you can keep training on that day since it doesn't advance the time (although this would be pointless because you are basically stuck here now anyway).
I tried to manually move ahead in the calendar and sim to my next scheduled training a week later but the game would correctly tell me that I have a fight and ask me what I would like to do. From there no matter what you choose it just brings you back to the date of the training and the fight and the pop up menu that tells you that you have a fight and asks what you would like to do.
If you try to simulate the training the day you have the first fight scheduled(not auto-simulate, but just hit simulate when you come to the day your training is on) the game goes into a perpetual loop where a pop up screen comes up saying "simulating fights. please wait." with the option to stop the simulation by pressing the A button. The only way you can get out of this loop is to time the A button press at the right time as the screen pops up.
Admittedly this whole thing is probably my fault. The email I got telling me the champ wanted to challenge me probably came before I scheduled a fight, but I wasn't checking my emails regularly enough since the emails in this game are almost always pointless and don't really contain any concrete information (not knocking the game as I love it, but the email feature is really a dud the way it is set up). Still, the game should have something coded into it to prevent this as it basically stops your legacy dead in its tracks. I can see it work in several ways: Perhaps you could code it so that if you accept a challenge via an email and select a certain date the game checks to see if you have a previously scheduled fight within a reasonable amount of time and asks you if you want to cancel that fight (with a possible accompanying hit to your popularity). Or, have the challenge come in as a pop-up on the main legacy screen after you finish a fight so that you don't have time to schedule another fight, thus avoiding the need to rely on checking the emails at all. Perhaps you could just have the game tell you that you can't schedule a fight so soon after another one and end it at that. Whatever the choice I'll be happy, so long as it doesn't freeze your legacy status in its tracks as it does now.
Sorry for the super long post..just wanted to communicate what was happening as closely as I could.
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