I actually prefer the CHR fail path there myself, I like MC a little off-balance, it contrasts nicely with Emily's poise there, and their reversal later. A lot of the checks are just the game reacting and confirming your play-style; whether or not you defeat Katie on the run doesn't matter much, except (as a character that boosted STR), knowing that you DID beat Katie. There are obviously a bunch of exceptions; events that are locked behind stat-changes, but those are almost never one-offs (so you can level up and go back later).
The one exception to that, and it's a low threshold because I didn't want to throw too many people off, is meeting Jalsa in the Dojo in Act VIII. That +60 STR check doesn't repeat, and for story reasons it only happens across a 24 day range (beginning of Act VIII->day 5 of Act IX).