I will say, I am a bit confused by the timeline. It sounds like the breakup with Darryl happened about a year before the start of the VN but the messages from Darryl and the flashback to the breakup both make it seem like the breakup just happened right before the trip to his sister's which also makes sense in that the breakup would be the catalyst to go visit his sister.
Which is it? I am leaning towards a year ago but the texts are strange. I am still going through at least so maybe it will clear up.
Overall fantastic!