TL;DR:
It was very hard to enjoy this show as someone who isn't a shut-in neet who is only concerned with their own feelings. I'm a weeb, but not an antisocial dork who is the epitome of "nice guys always finish last" or incel activity.
Not saying that if you like the show you're someone who fits that description, but if you truly relate to the self insert character that is 8man, you probably do fit that description.
In my opinion Oregairu is nothing more than a self insert story. It is a fairly well executed story as its so widely loved by losers who "Live in a society." But for an introvert without a superiority complex, I found it hard to get through the first season of this show.
-BIG FAT SPOILER-
I truly predicted the outcome of the show from the first episode, and was right. This isn't something great for a romantic drama that is supposed to be super deep and well thought out. If it were super deep and well thought out, there should be opportunities for the viewer to question a character's feelings towards another in the same way Hachiman does, but you can't, there are no seeds of doubt to be planted as everything is predictable.
-END OF BIG FAT SPOILER-
All of the character's main intentions are laid bare in front of the viewer, and then painstakingly elaborated in ways that counterract previous statments and often sound comically pretentious.
The humor in this show isn't something that will make you laugh out loud and it typically sticks to the same format of "witty" jokes and situations you've seen in plenty of other typical Rom-com animanga.
Most of the characters as I've already stated, are pretty devoid of realism to actual high school actions, this show doesn't accurately portray highschoolers, mostly exaggerated character tropes that seem to be tried and true for both japanese and western audiences
