Ruberick

Spice and Wolf has my favourite couple and best portrayal of romance and love not only in anime/light novel (Both are great), but in all of the media I've ever seen.
Nodame Cantabile is also pretty good, Kids on the Slope is very organic and genuine and Chihayafuru has less focus on it, but really great characters. All of those would make my top 50 Anime ever.
I liked toradora, but also less for the romance and more for the characters and humour.
On the topic of High School VNs: I try to mix it up and read High school stuff only with a considerable gap inbetween. (At least when the school and typical school tropes make a lot of the VNs read time) There are some that I genuinely like and recommend, like Chrono Clock and Daitoshokan no Hitsujikai, but a lot of them feel lazy, tired, repetitive...

Picking one of the games that didn't even try would be easy, but if the game doesn't care I don't see why I should.
From the games that actually did try I had the worst time with Amatarasu Riddle Star.
It was confused at best and a completely arbitrary mess at worst. (Which was kind of the point as an Alice in Wonderland story, but it's hard to care about characters then, which also aren't very inspired, slapping some tropes onto loosely based on Alice in Wonderland characters. This one didn't work for me at all and I believe it's misguided as a Charage VN.)
Too bad Hajimete no Okaa-san doesn't make the cut by a year, that one would have been an easy pick.

It would maybe seem like a good fit, but all of the anime I listed are actually nothing like toradora and the discussion here had to some extent shifted towards romance in general, which is why I just threw some examples out there of romance anime which tackle different angles of the spectrum rather well. (In contrast to toradora which was mentioned here as well)

I haven't read that many, compared to some of the veterans
I've read one of the older PeasSoft's titles - Koi Iro Chu! Lips. While it was filled with popular tropes, I still enjoyed it, because they executed those tropes reasonably well, and I liked the characters. So I guess that's how it is with me - I'm okay even with seemingly overused tropes if they are executed well. It's a problem however, if the execution itself is also lazy.
 
On a side note - recently I browsed my reading history on vndb, since I've been filling out start and finish dates. It struck me, that in 2018 I've read over twice as many VNs when compared with 2019. Incidentally, 2019 was the year when I started reading untranslated titles. And I guess it shows how much slower I am when reading in JP compared to EN. "Medium" sized VN would typically take me around a week when reading translated, but untranslated it can easily take one month or more - it takes around a week to finish one route

I don't check Verita yet, although looking from other Eushully VNs that use MTL, there's a chance that it night not worth it especially if I remember Soukoku no Arterial here. So yeah just don't play it, because you'll have a hard time to understand the dialogue from text alone if the narration translation is really bad.

Maybe that was poorly worded. I meant to stress unreasonable. A nukige can have a lot of (in-universe) reasonable h-scenes, but when the protagonist shrugs of being raped like mosquito bites and an orgy bus freely drives through the town, then it's pretty hard to take one of the heroines depression and coping after losing her boyfriend to a terminal illness seriously. It just creates too big shifts in tone.
Sure, go for it given the opportunity. I wouldn't give a cent for this in hindsight, but opinions are still just opinions and I'd be interested to hear thoughts on this, especially from people who have read a lot of VNs allready and will recognize the (lazy) tropes that are used in this one.

It's extremely hard to make me emotional, but I'd still like to make my case here. I usually don't tear up, I rather get pangs of satisfaction along the lines of "Thank you for blessing me with this powerful/well written scene". Rather than tearjerky they are generally more like memorable scenes for me.
Those include:
Saya no Uta (A very recent read, so it might just still be relevant for me)
Shining Song Starnova
Family Project
 
The only VN that actually made me tear up was Harukoi Otome, but I think that was more related to my state of mind at the time I read it and it's basically my proof for not being a robot. 
 
For some reason backstories in general have a harder time to impact me, the disconnect of time and seeing the results they had beforehand often takes the edge off for me.

I'd say not liking characters is a valid reason not to get romantically involved with them. 
Not sure if you're joking about the special ending. 
 
For what it's worth Rika was surprisingly second best girl after Misaki for me. Her route doesn't have many scenes to blow you out of the water, but it feels really genuine.
For me it felt like Misaki was the center of the VN, she had the backstory, she had all the impactful moments, she even had a fangirl to make things even more about her, so the competition was kinda rigged from the beginning.

Just wanted to stress, that it is a decidedly parodistic comedy VN and if it has the choice between taking an emotional story scene to its conclusion and making a joke out of it, it will opt for the later. I haven't read Lamunation so I can't make the comparison yet on how things are done there, but I have read Fureraba and it felt very different in what the VN set out to do, since Fureraba tries to be fun in a wholesome slice of life kind of way (mostly) and Sankaku Renai (mostly) pokes fun at story/setting/character tropes of charagames, (and otaku fandom in general) while going through the motions of being a super basic charagame itself. The intent (as I perceived it) was pretty different and that was the main point I wanted to make, sorry if I make it more difficult than it needs to be, but for me that's an important distinction.
It correlates to charage like Undertale does to classic RPGs and Bakemonogatari does to harem anime, but without having as much insight and instead having fun with the theme in general.

This one is super spoilery, so only open if you won't play it blind under any circumstances and need that info to decide.

That game and its sequel are indeed absolutely phenomenal. Unfortunately I could not place them in my list.
These are good recommendations. I happen to have already played the corresponding routes on them, so I can indeed say that they're quite good.
These are good!
I'll look into My Fair Princess.
For Hoshi Ori I'm technically in the middle of playing it right now, but it's not going all that well, hence this thread.
Wagamama is one of my favourite VNs ever, but there's just one route I haven't played that I'm leaving for a rainy day. Ashe's.
Speaking of which, you didn't recommend Ashe??
This one I did not know about. Is it a long route?
Sorcery Jokers is good for a variety of reasons, but romance was not one of them, I thought. In fact, the H-Scenes in this game actively infuriated me. They felt so different and extreme compared to everything else. That may have coloured my perception, though, making me think the romance was bad when it was only the final epilogues that were.
At any rate, this was already on my list.

Was hesitant to recommend this at first, since there's a somewhat blurry line to the consent, but I saw you played Bunny Black, so I'm going to do it anyway since this one is more wholesome than that.^^
I mentioned the sequel and this game in the What are you playing? thread. https://www.dlsite.com/ecchi-eng/work/=/product_id/RE240947.html
The dungeon of Lulu Farea has a large cast of girls, many Tsunderes and Kuuderes to be had in these two games, but there's only a fan translation to the second game. The blurry line definitely develops to mutual feelings in all cases, of that I can assure you. Also it's one of the most addicting puzzle games I've played. The Protagonist is even a weird/eccentric character who is an outcast (by choice) and they strangely gave him depth by making him shallow. 
Chrono Clock and Daitoshokan no Hitsujikai have some of the best casts of heroines in my opinion, but they are more witty and sharp-tongued than tsun or kuu. (Chrono Clock has a classic Tsundere and a somewhat kuudere heroine)

Yeah, my spoiler gets into some details about the gripes I had with the androphobia, but you don't want to read that yet. 
I've stopped minding incest stuff in japanese media a long time ago. Many charage also do a poor job of it, but I can't stop myself from going through every route anyway. I'd hesitate to call the sister route in this game a good portrayal of this relationship trope, but I'll at least call it one of the better portrayals within VNs. At this point I prefer it if they go balls to the wall not giving a damn about it, as in Imouto Paradise, so you can enjoy some cute girls without thinking too deeply into it. 
I think the stepmom would have been better as well, with the teacher/student angle on top it would have also had a lot of angles for conflict. Oh, well.

I guess it's a form of risk management. I'd draw parallels to the Imouto Paradise series or any longer running Lillith series. Nuki can get away with making the same game with minimal risk, using the same engine, layouts and staff. It's efficient and if the first game was a commercial success, the likelyhood of more games bringing in a stable income is better than risking your assets on something new/daring. Especially when you are expected to go in a specific, fetishy direction you don't want to lose your audience.
The Iberian peninsula is pretty much Spain and Portugal these days. Since Edel means regal in german I always took Edellant to be an euphemistic portrayal of germany or a germanic group of nations, with lant as a missspelling of Land. (Country in german)
 
As for my last games, I played Demonic Nation Florehades, it's more of a dungeon-crawling puzzle RPG-maker game, but so enjoyable that I have to mention it anyway. It's the sequel to Demon Cave Lulu Farea, where the protagonist is Klurs, a misguided human who tries to get into intimate relationships with monsters, after he failed to do so with human girls. He taught himself fighting moves that will only incapacitate others, without leaving lasting effects otherwise and he tries to make the girls he encounters into his girlfriends/wives. After he defeats a girl he will "rape" her, the quotation marks mean that he isn't violent about it, or strikes somewhat shady deals with the girls before the battle, making it either borderline consensual or comedic in nature. I would poke fun at this, but the game is very self aware and does that enough on its own.
The games system let's you freely traverse deeper and deeper into the dungeon with much freedom on how you tackle the puzzle element. You basically have attack and defense stats and every enemy has those as well and you deal excess attack to the enemy HP and they deal excess attack to your HP, making the whole process very predictable. You have to traverse the dungeons tackling enemys you are able to, getting stronger and engage the new enemies that you become able to defeat. I found that to be a very addicting, rewarding gameplay loop and super enjoyable if you like puzzle games, that's why I'm highlighting this game to this extent. The monster girls are very likeable, but the game is even enjoyable if you skip the H-scenes. I'd recommend starting with the first game, since it left you on a cliffhanger that is now finally resolved. Had a great time with this one 8/10
 
I took a break from Yumina the Ethereal, it's an enjoyable game so far, (I'm in chapter 4) but the dungeon-crawling segments are extremely tedious and my game completion OCD stops me from skimming them... I really like the battle system on the whole, but I don't think it's meant for longer grinds, since having skills that are largely dependent on each other and a steady fluctuation of skills you can and can't use, means every turn has to be thought through. Even when you grind through low-level enemies you can't just spam an attack, as you would in most other turn-based games and that really wears you down over hundreds of battles in the training segments.
 
So I went back to VN's. I read the first two episodes of 9 - Nine and it was a good experience overall. The dialogue has a pretty good flow and the characters have unique likeable traits. The first episode ends a bit weakly, not having much of a climax and just ending arbitrarily. The heroine is a pretty typical genuine good girl, they try to spice it up by off-setting her rich girl archetype with being frugal, good combination overall.
The second one has a better arc structure, in terms of impact, but some of it just feels like going through the motions of getting back up to speed. The sibling relationship is surprisingly well done in terms of build-up, chemistry and reluctance/reasoning for and against it.
The episodes are short, making them easily digestable, but it does feel like I only got a part of a complete visual novel, where everything is part of a multiple route mystery, so I left this story unfulfilled. That could be argued to be a good thing, since it means I wanted more of it, but it's a bit cheap nonetheless. I don't feel like rating it is appropriate yet, I want the complete picture before I do so.
 
With that done I felt up to read another Palette VN, hopefully getting a complete experience this time and started Koi ga Saku Koro Sakura Doki. This one felt like they really didn't know what to do with some of the characters, or even the general direction of the plot. I liked the protagonist, he was sensible and had an altruistic nature. Sadly that also leads to less potential for meaningful conflict.
This VN was a lot longer than necessary, they ran out of meaningful things to say, which resulted in too many boring stretches during the read. 6/10
 
Guess I'm gonna read Kyonyuu Fantasy 2 now, for some unapologetic dumb fun. Also have Newton and the Apple Tree installed, incase the Nuki overwhelms me. 

I've recently finished Kyonyuu Fantasy and its Gaiden fan disc (aka Funbag and Sideboob). Those were some real oddballs. Originally I tried the first one in Japanese years ago, but didn't like it and dropped it. When it got translated I gave it a new chance and read a bit occasionally. Still wasn't really convinced by the routes and was close to drop it again. Then I progressed a bit further and noticed that the real meat of the story is actually hidden in the harem route. That was rather unexpected since in most eroges (and not only nukiges) the harem routes are crap. I then continued right afterwards with Gaiden and finished that almost in one go. Having played both now I think I have a better picture of the series to accurately comment about it.
The Kyonyuu Fantasy series is pretty much a fantasy parody around a very 'potent' looser protagonist who goes from zero to hero. While this isn't an unusual setting, there's an unusual heavy focus on story and character development. The fantasy world is surprisingly rich even for non-nukige standards and represents a medieval Europe setting with fantasy elements. There are several factions, with each having their own representative key characters and soldiers, and all of them drawn and voiced. This also includes an unusual high amount of male characters, with several of them even playing key roles in the story. And not just as villains, the world is surprisingly grey here. Many characters have their own beliefs, strengths and weaknesses and some might even start out as enemies and then turn into friends later on.
There are frequently multiple interwoven intrigues going on. The similarities to medieval Europe are also striking, there's 'Fronce' which is clearly France, Spain is also mentioned as Iberia (?!) I think and even the Vatican plays an important role. Edellant itself seems to be a splinter state of the Holy Roman Empire, although the HRE probably doesn't exist as such in the game.
That said, while the series definitely has some commendable merits, it also has its fair share of weaknesses. First and foremost, the titles have a strong B-movie feeling that can be a real turn-off. All the characters are voiced, but certainly not by the best voice actors the scene has to offer. All characters have sprites, but they've usually just one pose and some look akward or even painfullly bad. The music isn't bad but some tracks are heavily overused and get very repetitive and annoying after a while.
The whole parody theme is also a bit of a double-edged sword. While it might make it easier to overlook some weaknesses, some characters and plot resolutions are also too silly and cheap and do more harm than good to the overall experience. Some characters also change too drastically during the story. The heroines in particular can go from literal hate and scorn towards the protagonist to almost worshipping him, appearing as if they would have been brainwashed.
This being tagged as a nukige is also a bit ironic, because it's arguably its weakest point. The whole boob-fetish of the VN is more often than not just akward or even gross instead of arousing. The art isn't the best and certainly one of the main reasons I've never seen those titles amongst the top sellers on Getchu. The backgrounds are decent, but the character art is very hit and miss. Luceria is probably one of the most ugly heroines I've ever seen in a VN while Gladys looks almost two art generations more refined. While the later titles do show some slight improvements in the art department, I think Kyonyuu Fantasy 3 (Athena) and Gaiden 2 After (Irina) are the first ones where they appear more significant. H-scenes also often appear randomly thrown in instead of being developped, especially harem scenes.
Heroine ranking: Gladys > Aphrodia = Emeralia > Isis >= Shamsiel > Nellis >> Roxanne >>> Luceria
Overall rating: 6.5/10 (KF) and 7/10 (Gaiden)
In general, I'm a bit irritated why Waffle insists to recreate pretty much the same title over and over again. They've good plot ideas and a very efficient usage of art - why aren't they striving for more? I'm sure that if they'd go for something more serious, they could reach a bigger audience.

Gave Chrono Clock a 8.5/10 recently, I liked it a lot, it had some unique spins to common tropes/heroine types and a cast of very lively and likeable heroines, definitely more of an easy-going, lighthearted VN with a pick me up atmosphere most of the time, but still touching upon some meaningful topics in an accessible way. A lot of "witty banter" going on, for lack of better words.

I guess it's a bit of a blurry line, but I remember liking kana - imouto and one or two corpse party game, ultimately doomed to fail, but at least trying in a way...
I thought Utsuge only defined the result, not how you got there and how you got there is the factor that matters for me most and why I hated Kira Kira.
Let me put it this way, I really connect to a struggle against inevitability, if the struggle only exists due to negligence and/or incompetence it becomes unbearably frustrating for me.

Gifting myself a VR set this year and looking forward to Spice & Wolf VR.
That's also pretty much were I hope gaming will make huge leaps over the next decade, so I'm getting myself set up in that respect.
Otherwise finishing the further education I started last year and getting a good paying job to buy all the state of the art gadgets our technical advancements lead to. Transfering consciousness might be a while off, but body augmentation wouldn't be too bad either, could be my only way to survive long enough for some good stuff that's coming further down the road, given my lifestyle.

Read a bunch of VNs again, first up Under one Wing:
I had some major issues with this one, most of them lead back to a shoddy execution in their world building. The VN never really explains about the past(something something war), the current economy (affordable aircrafts possible), not even how the dogfight sport that enjoys massive popularity is even played (rules). With that kind of limited knowledge, every event that takes place loses either believabilty or impact. The tournament that everything led up to feels very anticlimactic without understanding the stakes of maneuvers etc.
It's like a child led the project, you can feel a general passion about aviation and the aircrafts, but not the skill to wrap it in a detailed/interesting story. The characters are generally likable, but the routes also lack direction and proper narrative. 4/10
 
Next up Noble works: 
Pretty much the opposite problem, it was very well executed, but the premise is a bit flawed. Complaining about charage were the protagonist joins a special school of some sort would be pretty hyprocritical, they are a staple and if you read charage you will know what you're getting into, so that's not what I mean with the flawed premise. Much rather it's due to him coming to the school, posing as someone else. The resulting conflict in the routes feels samey, because it's repeatedly about his identity. Sometimes less is more, this VN would have been better with less heroines, even though they are generally likeable and for the most part different from each other. (Again, can't really complain about ojou-samas, if that archetype isn't for you, don't play this game) 
Still, I had a good time with it. 6/10
 
Easily the best out of the three VNs I've read, Chrono Clock:
I'll start with pretty much my only gripe, the mainstay of this VN, the time rewinding clock is severely underused. This VN has a clever, pragmatic protagonist, something I generally like, but the routes fail to give him opportunity to use the clock in a meaningful way most of the time. They are still good though. The heroines are genuine, distinct and fun to be around. The scenarios are either relatable or understandable and also have unique plot lines or at least unique resolutions. Everything is concise when it needs to be and funny when it can be. I usually don't comment much on technicals, like engine, sound and visuals, because I'm not very demanding in that regard, but I really liked the CG's in this one, they are very vibrant and detailed.
So, all in all, this one was pretty good. 8.5/10
 
Now I really need something with more gameplay, just started playing Yumina the Ethereal and Demon World Country Flore Hades (That one is more of a puzzle dungeon crawler though, with some rance vibes). Liking both of them so far.

I think some of our japanese readers could answer more accurately, but I think VNs tend to use the general gakko, which means school, without further specifying it, more frequently. Chugakko would be middle school and kotogakko or short koko is high school. Pretty sure I'm also frequently hearing koko, especially when characters are talking about other people who are attending a different school. (Basically when the characters need to be specific)
My take is the casual tone within ones school leans towards gakko and the tone when misunderstandings could occur leans towards "something-something" koko. (Or in rarer cases chugakko, maybe when the protagonist has a little sister that is still attending middle school, or just joined from a middle school)

As far as I know schooling begins with 6, then there are 6 years elementary, 3 years middle and 3 years high school, so the characters in pretty much every high school setting VN could only be 18 if they are in their graduate year or if they have repeated. In Japan pornography with underage fictional characters may be looked down upon, but since the age of consent is 13 in japan, all of the high school and most of the middle school stuff is pretty much save from every angle.
For localizations sake you could say that all of them started school 3 years late, early localizations (A lot of old JAST stuff) placed obvious high schoolers into universities in name only.

I usually don't use one for the first playthrough and just see where I happen to end up, if I liked the choice process of the game I may even go for a few more times while savescumming, in predictable moeges I try getting the (expected) worst girl first, then my completionist OCD kicks in, I look up a walkthrough and play all good/neutral/bad endings, get every CG and often I even read the sequels/extras/spin-offs to the VNs I didn't even particularly like, repeating the process... Don't be me.

Being a VN fan is suffering, because to enjoy it wholeheartedly you first have to accept your own shit taste. Luckily I've accepted mine a long time ago. 
Funbag Fantasy 2 is coming out soon, right? 

I've allways been into literature, film, video games, pretty much any medium for story telling. VNs are just another one of these for me and my interest in any of them can wane for a while and suddenly return with a vengeance or vice versa.
Maybe I'm easily influenced, but when I stumble across a work that is exemplary for why I grew to like that medium to begin with, it reignites a passion of sorts and I'll start to crack down on the respective backlog I have for that medium. 
For example, most recently that would have been return of the obra dinn for video games, while movies are currently on the backburner, except for maybe a marvel movie here or there.
Otaku related material may often come with inferior story telling and I can understand growing out of them. It still allows for a different kind of experience than other media and sometimes that's exactly what you want/need.

Family Project, pretty old, may not hold up too well, but I remember it fondly for very distinct heroines and interesting power/character dynamics.
Dangan Ronpa is pretty special in many respects, no H-scenes and the interactions with the "heroines" are pretty limited, but still fits your description I'd say. If you haven't played it just do yourself a favor and try it, I love these games.
Dracu-Riot urban fantasy, hit or miss depending on your tastes in setting I'd say.
Sweet Home all out nukige. Strong, independent, adult women who firmly take a hold of their sexual life are a rarity though, so I can't help wanting to mention this.