Thanks for the input. I do actually like darker things. Watching the movies they felt more like a horror than the fantasy/action of the other media out there, but I do make a distinction between dark and depressing and HF sadly lays both on thick. XD
In regards to point 4, that's very fair and I can see your point, but I also can't really bring myself to like Sakura. I feel sorry for her and all, but with HF also being the final route and the 'canon' ending for lack of a better term, I can't help but feel the whole tone is kinda regressive. Like Artoria is a literal dragon knight that can kick ass all over and while Rin is tsundere incarnate, she's also a very strong character. Sakura by comparison so far comes across as very Yamato Nadeshiko and damsel-like and that feels somewhat worse when Shiro is seemingly willing to give up not just his raison d'etre for living the past decade, but potentially the lives of hundreds if not thousands for it. If anything I feel like Fate/Kaleid did it better by having a very dark and seemingly hopeless situation, but also not having the protag give up on their goal and instead striving to achieve the impossible. Yeah, it might come across as naive or idealistic, but what is fiction for if not indulging in the impossible?
I dunno, maybe the third movie will change my mind and conclude things well, but I can't say yet. I would've liked to have watched the third, but I'm watching them with my nephew and he's a pleb who doesn't do subs.