Would this lead to not underestimating non-enemies outside of battle?
Cause just taking the capabilities of non-angelic/demonic beings seriously gets us like halfway to the Death lesson.
Basically my take is that in addition to creating plot hooks for future character interactions each option for a mission gone wrong and resulting Lesson addresses a flaw of Bartholomew.
If you choose Rowena then Bartholomew got humiliated by a human with some magic tricks** which forces them to admit that even though an Angel is on paper OP that doesn't always translate to a martial win against 'Lesser' foes.
If you choose the failed negotiation with a Reaper option then Bartholomew is being forced to confront the fact Heaven's antics have built up bad blood, organisations etc aren't going to just fall in line now the appearance of Heaven as an invincible superpower has cracked. Subtlety is required going forward.
** This is a somewhat rude-dismissive way to go about thinking about a powerful witch with 300 + years of experience but that's kind of the point.