So if Ji-ho is the male lead of the 'web novel', then it seems like Chunyoung is our lead. The pairings are pretty clear-cut so far, this doesn't feel like much of a harem aside from the web novel preface.
With Dan-I's hair color changing, I wonder if the author is going to make her more distinct looking. I like Dan-I's look but the side characters always comment on how plain she is.
The time skips are between the first year of middle school and the start of high school. Dan-I entered the web novel 3 years ago so we're just getting all the relevant events before they begin high school in the present.