Alright, I’m finally making the list… The anime within a group are just in alphabetical order, not ordered by difficulty. It’s also been a while since I’ve watched many of these (started watching anime with Japanese subs March of last year), so take these groupings with a grain of salt.
Very easy:
- Itai no wa Iya nano de Bougyoryoku ni Kyokufuri Shitai to Omoimasu.
- Karakai Jouzu no Takagi-san
- Maou-jou de Oyasumi
- Yuru Yuri
Easy:
- Akebi-chan no Sailor Fuku
- Gabriel Dropout
- Go-toubun no Hanayome (maybe medium, don’t quite remember)
- Koe no Katachi (maybe medium, I don’t remember)
- Love Live! School idol project
- Love Live! Superstar!!
- Mary to Majo no Hana (maybe medium, I don’t remember)
- Nakitai Watashi wa Neko wo Kaburu (maybe medium, I don’t remember)
- Non Non Biyori: Nonstop
- Shoujo☆Kageki Revue Starlight (but I had already seen this and knew the characters and story, so maybe medium)
- Sono Bisque Doll wa Koi wo Suru
Medium:
- Ano Hi Mita Hana no Namae wo Bokutachi wa Mada Shiranai.
- Bocchi the Rock
- Demi-chan wa Kataritai
- Kokoro ga Sakebitagatterun da.
- Komi-san wa, Komyushou desu.
- Mahou Shoujo Madoka☆Magica (I had already watched it three times before watching it with Japanese subs, so I may be understating the difficulty, not sure)
- Mahou Shoujo Madoka☆Magica: Hangyaku no Monogatari
- Ousama Ranking (often easy, but occasional spikes in difficulty pushed it up to medium)
- Sora yori mo Tooi Basho
Hard:
- Bokurano (medium difficulty much of the time, but spikes in difficulty whenever there were scenes with government people or heavy sci-fi scenes)
- Saiki Kusuo no Ψ-nan (they talk very fast in this show)
- Violet Evergarden (medium difficulty much of the time, but spikes in difficulty during military discussions)