I am currently running it and I am absolutely not sure how to get everything neatly together. It is an absolutely great campaign but here and there (at least to me) it gets quite hard to run.
The very first Game that i ran as a GM was a horror One-Shot. The very first boss fight there ended with the Bard insulting the guy to death whose job it is to pull peoples souls out of their bodies using echanted hooked chains.
Having an NPC write a love letter sounds to me just like having the guardsman tell everyone how it is his last day on duty and he can't wait to retire to sit on the shore of his favourite lake and fish in peace.
Would be a shame, if something... happened to them.
I tend to always ask so the Bard at least has a chance to use Cutting Words. Same goes for Light Domain Clerics.