Much like with Zoku (aka the 2nd season), Kan feels like it's starting to fall downwards from the high trajectory the first season gave it. Hachiman while initially a brooding edgy teenager who one way or another faces consequences because of how he goes about things, has slowly become a protagonist that people want to become/self-insert just because he gets chicks with minimal effort and staying brooding and edgy. While I do think this trope is fine, the execution is a critical part of this; as well as the overall premise of the story. The environment of the overall story is that it takes a more serious and pragmatic tone compared to the happy-go-lucky not-to-be-taken-seriously high school dramas present in many anime; yet Hachiman's characterization starting from Zoku and solidifying in Kan inclines me to think in a way that the series should be the latter. A clear contrast between the story's premise and the way Hachiman is written is what makes this anime difficult to actually consider "more serious" than other romance anime. Yukino on the other hand felt too passive compared to her more aggressive, stoic facade in the previous seasons. She however falls flat because of both the premise and how she becomes overall stoic and passive despite internal and external conflict and never really getting anything out of it other than a sudden realization which leads to the conclusion.
While the light novel might be able to make light of a lot of the series' issues, as well as should be cutting the studio some slack because it cannot adapt the entire novel, I still think that it's still important to keep consistency as to how this is received by others. Setting an entirely different tone from the previously established tone can devolve many of the characters into caricatures instead of decently-written characters. I do think however that all things considered, OreGairu is a decent anime; but the way it is advertised can be very confusing at most as the tones of the 1st season going into the 2nd and 3rd is a drastically different approach. However this shouldn't be a deterrent to stop someone from watching this anime. If you happen to like turn-your-brain-off romance anime (because we all need a little bit of escapism in life) then this will definitely be a great watch, otherwise it's not really as unique as a lot of people say it is.
Pros
+Decent soundtrack
+Very great art design
+Has a very heartwarming ending
Cons
-Steers clear of its original traction (i.e. a "serious" romance in the 1st season and a turn-your-brain-off romance anime in the next 2 seasons)
-MC devolved into a terribly-executed self-insert MC
-Heroines have little if any to contribute to the ending
-Story is being driven by plot and not by the characters
