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About School Days:
This is indeed a deeply flawed show and a lot of people hated it. However, a lot of people loved it too and it is indisputably one of the most unique anime ever. The fact that it has generated such strong feelings from so many people is indicative of this. It's one of the purer deconstruction anime and it basically deconstructs the idea that a normal guy in a high school rom com harem situation would act like an indecisive and asexual nice guy rather than trying to take advantage of the situation(what the MC does). I'm not gonna say anything more about the plot because that might be a spoiler.
Personally, I would still recommend watching it just because it's so unique and so many people talk about it (also free on Crunchy Roll). It also does mostly focus on the central three characters but it' very possible that you might still find these characters shallow and undeveloped. You definitely will feel this way about some of the side characters.
However I can say that based on your other reactions, I'm pretty sure you will like Fate/Zero and probably Full Metal Panic as well (personally I thought FMP: The Second Raid was far better so that's another awesome thing about FMP is that it has a sequel which is even better).
As far as where to go next, based on your appreciation of Crest of the Stars you might give some old Yoshiyuki Tomino a try namely the old Gundam series (the best being, in order, Zeta Gundam, Gundam 0080, Mobile Suit Gundam and Victory Gundam) as well as some other series (Space Runway Ideon and Aura Battler Dunbine). You might find the characters in these shows too dumb to relate to, a common complaint of Tomino series. Then again the plots are epic a la Crest of the Stars and the shows are definitely moving because of the high body counts (of main characters not just in general). Tomino's nickname is Kill Em All Tomino, for obvious reasons, and this means that his better works are mostly quite moving.
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