You need STR/CHR/INT of 10, then make sure you don't re-use the same tactic twice in one combat.
https://itch.io/post/1153047
Yupp; there's essentially 3 'story' events. The first is Black Rose II (triggered at night in the cafe). The second is Snowdrop's Adventure (triggered from Crowley in the evening, after your first upgrade). The Third is the Fae Lady (triggered from Crowley at Night, once you've upgraded it far enough). In addition to that there's a bunch of side-events, slice of life events with Dylan, Emily and Olivia, as well as upgraded dialog when you rest in Elsewhere.