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You need some time, check Quest Log for how much days left for next expansion or what you need to do.

Oddly, it never showed in the quest log. So I have just been going off of checking every day.

Strange, my Event Log shows Bareshade's Expansion fine, maybe it's a bug? Try to check Bernard's talk 14 days later to see if there's new expansion dialogue. I don't know if you need to processed stories to certain point because I started build Bareshade after I finish all the Event.

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It is still working, which is good, maybe it is just that it is an old save?

Maybe, I started play this game when 0.30.4 come out, so I don't know old save's compatibility, at least my 0.30.4 doesn't have any problem so far.

Hyao I think said to try and not use any old saves because they will prolly be buggy... So pretty plausible that's why.