Glad to see your diving in the typemoon verse, If you start watching fate; start with fate zero, then choose whether to go with the original fate staynight or unlimited bladeworks. Once you have those two under your belt check out the 3 heavens feel movies which must be watched in order. The dubs are also amazingly done so consider watching them. As for main characters Shirou Emiya, Rin Tohsaka, Artoria Pendragon (saber), Archer, and Kirei Kotomine are the characters in staynight, unlimited bladeworks and heavens feel. If you're getting confused on the intros its's because this entire series is based on a game that has multiple routes and each story had different endings for each character, some more sad, horrific (Heaven's feel is the darkest and most saddest) Staynight is less sad. As for who the villains are, that's from a certain point of view for some of them but you'll figure it out.
Fate hollow has action but has the most slice of life content and is only in visual novel/manga form on pc,ps2/vita, if you need help getting that I can hook you up. Fate hollow should be read after heavens feel. Finally unlike the other routes of the staynight/zero verse most characters have a good ending in this alternate dimension.
Today's menu for Emiya family is a wholesome slice of life / cooking anime/manga series. It contains a few parts from hollow and others. Check this out after you watch all of zero, stay night, unlimited bladeworks, and heavens feels.
Carnival Phantasm is something you shouldn't watch until you've watched all of the typemoon verse. It's a comedy/ slice of life series involving all the characters interacting from every type moon property.
Fate Kaleid is a magical girl spin off series about the young girl you've seen many times named Illya and um... well it's certainly not for me and I don't see you as the type to watch it either lmao. It has it's moments but I didn't enjoy it as much.
Please check all the fates I mentioned here as those are the most interlinked. Eventually you'll have stuff like the Lord El-Malloi spin off (which takes places between zero and staynight) Apocrypha and others.
Finally, you definitely want to watch Zero first otherwise a great many things get spoiled by stay night. If you want my personal opinion, watch stay night after zero then unlimited bladeworks and finally heavens feel. Again I recommend the dubs, they are just too good to pass up.
Once you finish the fate verse I recommend Kara no Kyoukai (garden of sinners); its a legendary anime series in movie form. Those posting comments please avoid spoiling anything and everything for Jet.
