Clannad and Little Busters I played right after Rewrite since they were made by the same studio. I'd say Little Busters was more enjoyable than Clannad, but that's probably because Little Busters had more of a mystery going on than Clannad.
We had a good discussion about Clannad a few months ago that's probably worth reading through. Clannad is surprisingly obtuse, but when you peel back the layers, there's something spectacular to see.
Let me outline the full story of how I interpret Clannad's ending.
I finished this one few weeks ago, and it was really good, but I've heard mixed things about the sequel (or the million sequels/spinoffs/gacha games?????)
I think it's better to spread out to the other parts of Type Moon first before going deeper into Fate. There's a lot of other cool stuff that adds much more to the setting than just "It's a holy grail war, but somewhere else, with different people." Kara no Kyoukai will teach you about the setting's underlying mythology and origins. Witch on the Holy Night can teach you a lot more about Mage culture and the significance behind two of the biggest recurring characters. Tsukihime paints a picture of super natural society beyond Mages. Stuff like the Church, Extrasensories, and Vampire society.
That being said, I can give you a big run down of the big Fate spinoffs just so you have an idea of what you're getting in to.
Hollow Ataraxia is half "Watch the characters you like eat pudding and play tennis together" and half "backstory for a few very cool but obscure characters that occasionally come up elsewhere for the sole purpose of confusing casual fans."
The Extra duology is neat. An alternate take on the same ideas with different characters in a more bizarre and creative setting. The combat sucks though and it's super grindy. If you play it, play it on emulator and have the speedup button essentially taped down.
The Extella duology is kinda cringe. The best thing I can say about it is that Scathach gets a teacher's outfit in the second game. Which was put there, by god, to appeal to me, specifically.
Grand Order is... hard to describe. The most consumer hostile game mechanics imaginable, as well as several hundreds of hours of dull content and boring storytelling are what separates the average casual Type Moon fan from a few of the most well written and inspiring stories Nasu has ever told. Lostbelt 6 is actual art. It is also the second most recent story chapter in a game that has ran in America for over a decade.
Verdict? Get a story summary from youtube, and ignore everything else. No matter how cool you think Muramasa looks, or how fat Musashi's milkers are. Ignore those, they can only make your life worse.
