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Fate/Zero is definitely worth watching but I'd wait on that because I technically find Fate/Stay Night to be the better entry point into the Fate/ series.
That would only be true if he wanted to play the visual novel. If he's only willing to watch ufotable's F/Z and UBW, then Fate/Zero is the intended first watch. With the way that UBW is structured, it provides reasonable conclusions to each of the common characters' central plot devices. ufotable's UBW assumes you've seen F/Z.
I don't know. I started the series with Fate/zero, and I stopped watching it around halfway. The anime gets really smurfed up. I'm not sure if that is the best introduction to the Fate series. I actually rewatched Fate/zero after /stay night and it went down a lot better now that I had context.
That's the thing about prequels. I've never seen the Fate series, so I can't comment on it specifically, but I always roll my eyes when people tell others to watch prequels first. Not only do you usually need context, but the drama is lost on you, because the drama usually stems from how it's connected to the original. It's like telling people Birth By Sleep is the best entry point into Kingdom Hearts :