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Would we need to redownload the latest version or is there like an update we can apply to our software?

At the moment you need to download the version each time

one last question. It appears that when you play the career mode that the game crashes after the entire month of may is simmed. Idk if you can do this also, but if you had it so you can sim a week at a time instead of by event that would be really cool. Just a recommendation. 

Thanks for reporting the issue and thanks for a great input which I hope we will be able to implement soon