And now for the question that keeps me awake every night.
How do people find this stuff cute?
That guy who does art for Key has always had a weird art style, but the weirder looking ones you've posted are from the earlier Toei adaptions of Kanon, which people generally regard as stuff. The later KyoAni adaptions have a better artstyle and better animation, but since they're still based off of the VN artwork they look kinda weird.
People generally give Little Busters a lot less stuff since it had this artist in addition to Na-Ga, who would later design the Angel Beats! characters.
Not sure about Rewrite, it seems like the art is better than Clannad's but I haven't looked at it.
And now for the question that keeps me awake every night.
How do people find this stuff cute?
Anyway, since I'm still in the romancish mood, thinking of watching Date A Live, Kaichou wa Maid-sama, Planetes or at a stretch R-15.
Suggestions on what to watch next?
I've been meaning to watch Planetes because sci-fi, but yeah Date A Live was a good choice (also I figure you'd like Yoshino).
Now you just have to wait for season 2 later on.