Well, the new update is very effective at what it does. Possibly too effective? It works very well at providing a sense of pressure, feeling how the winter slowly wears everyone down. Narrativly I have no issues with it, but the gameplay aspect is a bit too fiddly for my taste. I have no head for numbers, and trying to play Civilization V in text format is not enjoyable to me. Spending so much time taking notes and calculating things kind of pulls me out of the immersion too.
That said, I can respect that having things too easy would break the immersion for other players, so this isn’t necessarily something that needs fixing. But as @cascat07 mentioned, I do think the results need to be more consistent to avoid boxing yourself in and having to restart. I’d suggest checkpoints but I expect it would too messy to implement.
As it stands right now, I found no way to survive the winter without stealing from absolutely everyone. If there is a way to do it, it requires far more careful calculation that I can manage.
EDIT: It also occurs to me this system is reeeeally not replay friendly - it’s very time consuming and if luck isn’t on your side it could potentially screw you for the entire game. It’s makes all the various branches rather moot if only one can be completed without crippling loses.