As someone who came from watching Fate / Zero first, Fate Stay / Night [Ultimate Blade Works] has a very strong start, following grown up characters from the prequel, now seemly being able to shine and fight in the next great holy war to overtake their predecessors. But after the first 4ish episodes, it just mostly falls flat because of two main reasons:
Being the adopted son of Kiritsugu (For the most part the main character of Fate / Zero), Shirou starts of being very interesting, seemly continuing his fathers legacy into the next holy war. But after you get to know him, he turns out to be a bland, generic main character with no interesting character traits and a very low grasp on magic. Because of this, almost every fight and situation he's in, all he can do is stand around, get caught or get hurt, just to need to be saved by someone else.
And you think he would improve on his magic or fighting skills through season 1, and while they try to accomplish this, he really shows almost no promise so far to be anywhere as interesting as a character like Rin, the other supporting main character. Rin carries most situations and essentially babysits Shirou through the holy war, which is just a pain to watch.
Another of the main issues which goes alongside Shirou, is the fact that almost nothing is progressed in the holy war for all of season 1. The entire premise of the holy war is to defeat / kill the other masters and servants, so you can get closer to being the last one standing. However Fate / Stay Night refuses to kill almost anyone, even characters that are barely important and have seen almost no screen time. This leads to important fights just ending with characters leaving, and deciding not to kill the other master, for really no good reason aside from they didn't feel like it. It would feel less jarring if they actually had valid reasons for it, but they just don't even bother to give them one.
Most fights are animated very well, so you can look forward to that throughout the show. And aside from Shirou, most of the characters are pretty decent, especially Rin, with characters hanging out being some of the most fun moments in the show. Its much easier to watch if you've seen Fate / Zero, as certain characters you already know being on screen can be enough for it to be entertaining.
As a first anime I think people would enjoy this a lot, but with Fate / Zero being my baseline for how interesting a holy war can be, Fate / Stay Night [Ultimate Blade Works] season 1 just doesn't do it for me. If you're interested in Fate, watch Fate / Zero.
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