I think this is my favorite so far of the lists you've posted. ~5 per category, roughly ordered by "noob-friendliness" is a good way to go. Particularly the inclusion of "Gameplay" as its own category is helpful to separate out games with elements beyond the usual read + make choices. Super information dense, but my eyes just passed over most of the symbols the first time so it's apparently easy to ignore the extra information if you're not looking for it. Besides not having read most of the works here, there's not much to comment on the game choices because they're largely the same in all these lists, so it's mostly the presentation of this version that I prefer.
I think for a branching / multiple endings game, the first route will always be the most special. Because at that point you'll be going in blind, to some extent. You may understand the vibe of the beginning of the game, and can extrapolate on the tone of the endings, but you'll never know for sure until you complete the route. You're forced to prepare yourself for the tonal shift that may or may not happen. And from that uncertainty comes a better payoff, in my mind.
For that reason I'll nominate my first ending of Grisaia no Kajitsu, Sachi.
Strange that this one recommends Euphoria without any sort of content warning.
It's probably better to play the standard Vampire: The Masquerade, although it is not a VN it is a story-driven RPG, and it's commonly regarded as a masterpiece in its genre.
Michiru is definitely a solid pick. That was my second route, and probably my second favorite too (I think I must give the win to Sachi though). I've only played about an hour or two of Labyrinth of Grisaia so far, and although I didn't think Fruit really needed a sequel, I'm interested to see where else they take it.
Tsukihime is definitely on my radar, every time I see the "not quite Saber" girl it catches my eye, in almost an uncanny valley sort of way lol. If the UX is approximately as good as Fate then it would be no problem, although it seems like it's not voice acted, which is a bit of a shame. I know Fate wasn't originally voice acted either, but to me the voice acting work is one of the best parts of the game.
In any case, it's always fun to see a dedicated fan of a single series, and thanks for your suggestion. And as a slight aside, I've still gotta figure out my profile picture for this site. I don't quite know what kinda impression I want to give yet =)
Having not delved too deep into attempting VNs in Japanese, I've only used the anime difficulty features, but I've found it to be useful for narrowing things down. In particular I first search for something I'm interested in, and if it's above a Difficulty 3 I sigh and pass it by =P
I'm new to lemmy, but I think we're trying to make a VN community happen over at visualnovels@comfysnug.space . This post is the first I've heard of Jack Jeanne, but with it recommended twice already I might have to check it out, although I'm not usually much of a console or handheld player. It could be a good excuse to wipe the dust off the old Switch though lol.
I was also a lurker on those subreddits, although I mostly just used the r/visualnovels suggestions list to help pick what to read.
Recently I finished both Fate/stay Night and The Fruit of Grisaia after many months (years?) of on and off reading. Maybe not an achievement in the traditional sense of the word, but in the VN world it feels like one lol. I was a big fan of the characters and somewhat flippant tone of Grisaia, and despite the lack of realism I think it still handles its subject matter pretty seriously. Perhaps it's an unpopular opinion, but I was a bit more critical of FSN, and I probably wouldn't recommend it unless you were already interested in the world-building from being exposed to the anime.
Although it's more of a total overhaul, I've been a fan of Requiem. It's more of a traditional RPG overhaul, returning to a static level based system (i.e. enemies do not scale their levels with you and will be much more dangerous at low levels). The time commitment of compiling a good modlist and setting up and debugging the mods has discouraged me from playing it recently though.
I've always liked this, it has pretty much everything you could want in a personal project: a catchy name and a whimsical idea that is just on the edge of being actually practical.
Key games are pretty safe, since there is usually nothing to censor.