Well, first, do you want to get into Type-Moon or get into Fate? Because they’re is a difference there because Type-moon has a bigger universe and Fate is one part of it. You just don’t see the other parts as often because Fate is their cash cow they’ll milk till it’s dust.

Now, if you wanna get into Tsukihime the OG VN is basically the only way until the remake. For KnK I’d recommend the movies over the LN. I’d also recommend KnK over Tsukihime due to how old it is.

Now I’m assuming you’re actually more interested Fate in that case the absolute best way to get into Fate is through Fate/Grand Order because it’s free.

If you’re more interested in anime to watch then Fate/Zero, Fate/Stay Night -Unlimited Blade Works-, and the Fate/Stay Night -Heaven Feel- movies are a good way too. If you wanna see the Fate route animated then you’ll have to watch the DEEN anime which isn’t regarded highly. If you don’t mind lolis then Prisma Ilya is an option. It’s probably the most divergent from Fate’s main “meta lore” but people seem to like it. I didn’t watch it myself.

I don’t recommend Apocrypha because it’s not good. Only watch if you’re really desperate for more Fate stuff. The F/GO OVA Fate/Grand Order -The First Order- isn’t worth watching because it’s pretty boring. The Fate/Grand Order -Moonlight Lost Room- you need to watch after completing all the Orders in F/GO because it spoils stuff from them and, also, serves as a prologue to the Cosmos in the Lost Belt “chapter” of F/GO (currently, only the very start of it is available). 

I’d put off watching Fate/Extra Last Encore or playing Extella until you’ve played/watched a playthrough of Fate/Extra because both reference/spoil plot element’s of OG Extra (and you can’t really understand some of what’s happening in Last Encore without the context of Extra).

I’d recommend the animes over the VN at least for everything but the Fate route but really if you play the Fate route you might as well finish them all.

As far as why there are so many Saber faces. It’s because Takeuchi (Co-founder of TM) is a creepy otaku who I’m pretty sure has mandated that all series include atleast one saber-face in any official type-moon series.

TL;DR: Play F/GO for the best entry way to Fate. Watch Fate/Zero, or Fate/Stay Night -Unlimited Blade Works- anime if you wanna watch anime. Don’t bother with the VN unless you wanna read. Or play the Extra game > play Extella > watch Last Encore.