Hi Milo,
1- This bug usually is usually related to using old saves. Besides from that, make sure you completed the date. You can't go forward (level 4 for example) if you didn't complete Date 1. Same with date 2 and level 7, etc.
2- The "time limit" on the next update will have no real consequences. It just an indicator so players can start feeling days as another resource. Nothing else. But in v1.0 it will have consequences. Endings will depend on the days needed. Doesn't mean more days = bad ending. Just different endings. We'll consider anyway if a "free mode" will be added once you unlocked 1 or some of the endings.
Thanks for the suggestions, but the endings are already written and decided. It's possible you will see something like that or not. Can't tell you ;)
Cheers!