FATE S/N UBW: 2x4 Reaction EARLY ACCESS

If he's not up for reading the VN (it is pretty dang long after all) he could always try out the DEEN version for the Fate route. Aside from the generally way lower quality compared to the Ufotable adaptations my main gripe with it is hot tried incorporating events from both UBW and HF, but it can't spoil UBW now that he's seen it and most of the things from HF it spoils have already been spoiled by Zero.

Simon Ovesen

Don't worry. There's no "everyone's saved" ending in the Fate Universe, not even in light-hearted spin-offs. Instead, there are many "everyone's F-ed" things. Btw, if you want to see the specific moment when Illya's blinded you can take a look at the uncensored version. Not saying anyone would enjoy it, though. You have to play through UBW to open the Heaven's Feel route in the original game, but they're basically different timelines during the same period like others have mentioned.

Kevin

The thing is Fate/stay night has 3 routes, each of them focuses on specific relationship. 1. Fate/stay night (Shirou & Saber) 2. Fate/stay night: UBW (Shirou & Rin) 3. Fate/stay night: Heaven's Feel (Shirou & Sakura) You can see them as parallel events with different female lead, but the timelines overlap. It is a loop repeated three times with different scenarios, the plot gets darker and crueler moving down the list provided.

ℂanny

Illya has a much larger role in the Fate route, not sure about Heavens Feel personally but yeah, everyone above pretty much covered it

KaedenKing

When the grail says "Angra Mainyu curses you" in Fate/Zero, it's not kidding around. The stress of a lifetime of killing and everything he lost, combined with the curse of the grail, meant that Kiritsugu unfortunately died before his time. About Illya and other characters: Remember that UBW is only one of 3 routes to the Fate story, and some characters get more character development and awesome scenes than others. Illya has the smallest pressence in UBW, so if you want the full story, i recommend reading the Visual Novel. Would be great to watch/read along with you too if you wanted to make videos of it :)