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found the setting
Ok, I found the setting that was causing this, but I don't know why it was screwing up so massively on both of our computers, as I can't imagine we're the only people that chose the following option:
Game Setup, Almanac Options, Archive HTML reports annually
Once I took the checkmark out of that option, I was able to roll from 12/31 to 1/1 without issue.
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