Manager Career Mode issues (compiled)

In season 4. Working from EFL League 2 from Prem League.

At end of season 3, I used the calendar mode to speed up the last few months. Season was a wash.  Soon after my star striker's morale goes to 0 due to no playing time (he did start though & had a good season) & demands a transfer.

Season ends, morale goes back to 100. Player is now happy. It was like it never happened. 

So, I intend to sell this player anyways. 85 rated player. Close a deal for 130,000,000 USD. Great deal. 

Only problem is that nothing else happened. Player never transferred. Never collected money. Closed two other deals. Agreements reached. Nothing happens. I needed to sell off the star players and reload at start of new season. It's part of the fun. So. I kept simulating games expecting something to give. Nothing. Just green checkmarks for accepted deals and no movement. 

Eventually I pass the transfer window. I was one player short of a full roster. Team was crap and now I was unable to make any move. So, I had to add a free agent. I added a free agent. This appeared to have "unblocked" the transfer issue for 1 single transfer. After that, back to "accepted" transfers with nothing happening. 

It's basically game breaking and whatever the issue is it persists in the saved season file. My assumption is that using calendar to speed up time somehow introduced a breaking change into transfer system. Restarting game and reloading save file does not fix. My only option now is to start over and use many save files to hopefully prevent it from happening again.