might be that you did something in a empty time spot that's in my WT, if you did something then it might of change what i added in, i don't even repeat old content that much, that's why there's a lot of the empty spots, but if you are skipping the empty time spots and still can't get it to trigger, best thing to do is
delete the FootOfTheMoutains folder from
C:\Users\name\AppData\Roaming\RenPy
delete the whole game folder along with saves
FootOfTheMountains-V8hotfix-pc
unpack the game again, get my save, move it over then start
every time when a new update gets release, i always delete the FootOfTheMoutains folder from C:\Users\name\AppData\Roaming\RenPy, so everything will be fresh and i wont have any problems