storyteller

One Last Time
Protag and a few friends (3~4?) wake up to find themselves in another world, where they must work together to survive and overcome hardships while searching for a way to return to their own world. With their teamwork, they easily surmount the various challenges presented against them, finally reaching their destination. However, they are told only one of them can return at a time. The rest will have to do it again from the start. You choose one of the characters to send back.
Protag and a few friends (minus the one sent back last time) wake up in the same world, with no knowledge of the previous loop. Once again, they work through the same hardships, though a little more difficult this time, and reach their destination once again. There, they're met with the same decision: choose a character to send back.
This keeps on going, with each loop becoming more difficult than the last as their numbers dwindle. In the end, with only two left, they barely make it to their destination. Both the protag and the remaining characters know that neither will be able to complete the quest on their next loop. The protag sends the last remaining friend home.
The protagonist wakes up alone, with no knowledge of past loops. He must brave the hardships one last time, but this time, there is no one to help him along the way.

It's that day.

And, of course, me being me, I couldn't be satisfied to just go pick up my game.

Seriously. **** my wallet.

Why you haven't yet watched everything Miyazaki is beyond me. He's the go-to for anyone looking into anime films.
A few of his that has yet to be mentioned: Whispers of the Heart (also occasionally known as Valley of the Heart, If You Listen Closely, etc.) and the recent Kaze Tachinu (The Wind Rises).
I know you said no, but I have to second The Girl Who Leapt Through Time.
And since you don't have either that or Summer Wars under your belt, I imagine you don't have Sennen Joyuu (Millennium Actress) either.
I just watched Kokoro ga Sakebitagatterunda today and I liked it, so I'd recommend that, as well.
Also know you said you wanted anime only, but I must recommend The Man from Earth.

RIP my room's lighting, but it's finally here~! Time to ruin my sleep schedule.
 

I should be translating Majikoi A-1, but I am on an amazingly extended period of zero motivation.
So here I am with yet another under-appreciated and untranslated light novel.
One Day, A Bomb Came Falling

    One Day, A Bomb Came Falling is an SF Anthology by Furuhashi Hideyuki, who won the 2nd Dengeki Award with his debut light novel Blackrod (Which is also an amazing light? novel).
    Here, SF is better interpreted as "sukoshi fushigi" rather than "science fiction". It features 7 normal-boy-meets-not-so-normal-girl stories.
    The End is something that can come about unexpectedly, on a day just like any other.
    That day, the self-proclaimed newest-model bomb that came falling reminded me of Hirosaki Hikari, a girl I liked in High School; a fact that made my heart flutter.
    --"One Day, A Bomb Came Falling"
    "One Day, A Bomb Came Falling", the title and first work of the anthology, tells the tale of Nagashima, a 2nd-year ronin  who is playing hooky on his cram school's roof when a girl that looks a lot like Hirosaki, the girl he liked in high school, comes falling from the sky. She claims to be a 50 gigaton-class bomb, has a "Heart-Pounding☆Doomsday Clock" on her chest that advances whenever she has romantic feelings, and will explode when the clock reaches 12:00 AM. She came seeking Nagashima to help her detonate so that she can leave a beautiful mushroom cloud (and obliterate Japan in the process).
    This year's cold gets you in the brain.
    Just this morning, the news warned of a terrible "Fool Cold" that was getting around, telling us we should gargle and wash our hands frequently, but...
    --"Grow Bigger!"
    In "Grow Bigger!", a common cold can cause you memory regression. Kogure's much taller childhood (girl) friend catches one, and seeing as her mother isn't capable of picking her up immediately, he is tasked with taking her home. A much harder job than it sounds given their height difference and the fact that she loses a few years worth of memory with each sneeze!
    In the past, I never believed in heaven or hell.
    But now, I know that these places truly exist.
    Where are they, you ask? Well...
    --"The Night of the Loving Dead"
    As the title may suggest, this story is about "zombies". In the world of "The Night of the Loving Dead", the dead don't stay dead for long. These former-deads, "repeaters", as Mamoru calls them, spend the rest of their un-life reliving one particular day of their life. In the same vein, Nagi, Mamoru's very own "repeater", comes to him every night and whispers to him,
    "E h e h e , t h a t ' s r i g h t , w e ' r e g o i n g t o t h e a m u s e m e n t p a r k t o d a y !"
    "Toto-kami-ja"
    "Seat Number 0"
    "Third Period with Madoka"
    Long ago, there was a huge war, and a lot of people died.
    It was about 60 years ago, that's four times as long as I've lived -- So, a thing long past, just the way Oda Nobunaga and Tyrannosaurs Rex are.
    Hara Michiko is just like them, a person from long ago.
    Unlike Nobunaga and Tyrannosaurs, however, she isn't on show at some museum. No, she's a living girl, breathing even this very second.
    --"Long Ago, A Bomb Came Falling"
    "Long Ago, A Bomb Came Falling" is a mirror of the first story, and the closing story to the anthology. In their equivalent of World War 2, Japan is bombed with a "Time Wave Bomb" rather than an atomic bomb. It completely obliterated everything within an 100 m radius, and wrought havoc over the 10 km radius beyond that, leaving one lone survivor at its center - her, Hara Michiko. At the epicenter of the explosion, rebounding time waves caused a 5 m high cylindrical space of "compressed time" where everything moves at 1/60,000,000 of the speed outside it. The main character, the grandson of the man in charge of the Memorial Park where she remains standing, spends his days thinking about her and nights staring at her.
 
I'll fill in the rest later.

It's WA2,
This one really needs context. He wakes up to find her not in bed next to him, goes around searching his small room, opening the curtains and being blinded (despite it being cloudy), then looking around for her clothes to find that some of it (the clothes by the pillows, one piece of underwear, and her coat) were gone, then finding her wallet? is gone. And finally coming to the conclusion that she's just gone to the convenience store.
He seems to be under the impression she (Chiaki) might up and leave him at any time.

Having been deprived of her source of heat (me), the other sleepyhead squirmed about for a while, but soon pulled some blankets over herself and fell soundly asleep.
Potentially "returned to her dreams" instead of "fell soundly asleep".

Lol. Primo is giving a very abstract descriptions of what caused her to end up "here", completely using only onomatopoeias.
W, well, I got *sfx being blown away* or something, *sfx being covered in mud*, *sfx being spun around*, and finally *sound of being pounded on the ground*, then found myself here.
I... don't think I'm going to be able to give you a concrete sentence for this one, lol.

Dear whoever-wrote-the-'Looking-for-more-Player-Mentors'-forum-announcement.
In a bid to improve my navigational e><perience on this forum, 'surfing' I believe is the modern term, I sought to remove the large, blocky announcement atop the boards proper. See I had already read it, and it was rectangular and coloured (when viewed through my awesome theme) a deep blue, which thoroughly ruined the aesthetics.  So, following your friendly advice I gently pressed the '><' button with the e><pectation that this eyesore would immediately vanish from my field of view.
Nothing happened.
I pressed it once more, and again nothing happened. What was this trickery I had succumbed to? I did not know, but whoever was behind this ruse didn't know who they were dealing with - I know how to deal with such situations. Force. It is, after all, the go-to solution for all tricky problems.
And so I began to hammer on the button using my forefinger with formidable gusto and strength, and when that didn't work I used my fist, and when that didn't work a hammer and after all this it still remained; still blue, still large, still... blobby. Sitting there at the top of the forum mocking my efforts.
Alas, I can no longer follow your suggestion, for I seemed to have driven an... object through the '><' button on my keyboard and it has sustained, erm, damage in the process of being... destroyed. You will note my '><'es no longer contain an '><' at all, and I have been reduced to dreaded leetspeak to appro><imate the letter in question. The agony of being limited only to 25 letters of the alphabet cannot be e><pressed in words. Pity me, for my troubles are great.
Yours in suffering, Rooke.
.......
PS: A good natured and guffaw happy friend has alerted me to my error. I have reread your above announcement and my blunder is now clear. Ah, yes, 'click with the mouse,' I now see where I went wrong. Please ignore all of the above 
PPS: I mean it, pretend it never happened  

Having been deprived of her source of heat (me), the other sleepyhead squirmed about for a while, but soon pulled some blankets over herself and fell soundly asleep.
Potentially "returned to her dreams" instead of "fell soundly asleep".

Lol. Primo is giving a very abstract descriptions of what caused her to end up "here", completely using only onomatopoeias.
W, well, I got *sfx being blown away* or something, *sfx being covered in mud*, *sfx being spun around*, and finally *sound of being pounded on the ground*, then found myself here.
I... don't think I'm going to be able to give you a concrete sentence for this one, lol.

Living in Japan, most everything I buy is naturally Japanese.
However I figured tonight's purchase was worth mention.

So, I decided to go and buy my first ever physical copy of VN.
What I planned on buying tonight:
Dies Irae or ChuSingra 46+1

What I ended up buying tonight:

Living in Japan, most everything I buy is naturally Japanese.
However I figured tonight's purchase was worth mention.

So, I decided to go and buy my first ever physical copy of VN.
What I planned on buying tonight:
Dies Irae or ChuSingra 46+1

What I ended up buying tonight:

頭にくる。
You make me mad!
 

It's that day.

And, of course, me being me, I couldn't be satisfied to just go pick up my game.

Seriously. **** my wallet.

It's that day.

And, of course, me being me, I couldn't be satisfied to just go pick up my game.

Seriously. **** my wallet.

It's that day.

And, of course, me being me, I couldn't be satisfied to just go pick up my game.

Seriously. **** my wallet.

Hikoukigumo no Mukougawa - Aya "end" is technically the bad end to Miina route. Except for the fact that it doesn't have a proper ending, it acts like just another character route... kind of.
Sengoku Rance - Ran bad (?) end. After seeing Rance being the jerkass he is, it's nice to have that one route where you can say **** you Rance!
Otomimi Infinity - If you attempt to complete the main heroine route before you complete all other routes, you fail your mission and end up in the intimately loving care of your sister. Surely a fate worse than death?
Doki Doki Majo Shinpan - Not sure if this counts... but if the MC fails any mission, he gets turned into the ultimate do-gooder, where he is literally incapable of doing anything bad for the rest of his life. And he'll be happy about it, too!
 

Since I've been meaning to put together a post on this for a while, given my own personal flailings in this direction, here's an attempt to answer the question. My post gives the benefit of the doubt and assumes you actually want to buy VNs, ideally supporting the developer that originally published it. Here's a list of all the options for that which I know of and have personally used:
- Many VNs are officially licensed by western publishers for release in the US, and often other English-speaking countries as well. MangaGamer, JAST USA, and SekaiProject (all ages)/DenpaSoft (18+) are the big-name publishers currently officially licensing and translating VNs. If you can find what you want in one of these places, this is the easiest, probably cheapest (short of pirating - see bottom paragraph), and certainly most legal way of obtaining a VN.
Assuming the VN you are interested in is not officially licensed for release outside Japan by one of the above, there are a variety of services for importing stuff from Japan. There are restrictions around exporting of 18+ materials from Japan, including most VNs, which is why importing is a bit sketchy, and why most VN materials are labeled "only for sale in Japan". However, there are still a variety of import services available:
- You can use a "re-shipper" like tenso (I have personally used their service a few times, no issues with them). A re-shipper gives you a Japanese address. Then can buy anything (including 18+ material that would otherwise only ship in-country) from retailers like amazon.co.jp, which very likely has whatever VN you're looking for, but won't ship it out-of-country. When your purchase arrives at the re-shipper address, they have you approve the package, charge you a fee, and ship it on to you. This combination is the cheapest importing option I know of, usually, because amazon.co.jp prices are pretty competitive. Naturally, you need to be careful of both the original seller and the re-shipper when using this strategy, so there's a little more risk associated than most other options.
- Mandarake, from what I understand, is a service that does online listing and sales of items which are for sale in a bunch of physical stores in Tokyo. I've ordered a couple things from them, never had any difficulties aside from problems using their search, and sometimes having trouble understanding what I was actually buying . This option is a mixed bag on cost, because sometimes you can get used items at a good deal, and sometimes you buy new items at a moderate or high price. It's a guarantee with this one that you will have to pay a pretty decent shipping price.
- J-List has a rather small catalog of importable games, notably including pretty much any all-ages release by Key (and also some others). Cost is very high, substantially more so than the above two, but in my opinion this is the lowest-risk purchase. Also, it has the easiest-to-use search for an English speaker.
A general tip for searching on any natively Japanese site, including both Mandarake and amazon.co.jp: you need to search on the Japanese title, or you won't find anything useful, and you should try various parts of the title if you're still having trouble. As an example, searching for "Comyu" on amazon.co.jp is going to yield nothing useful - if you instead search the Japanese sub-title, "黒い竜と優しい王国 -", you'll easily find what you're looking for. Rule of thumb: just look the game up on VNDB, copy the Japanese title below the English title, and paste that for searches on amazon.co.jp and Mandarake, or any other Japanese site you may find for purchasing VNs.
 
Finally: if you want to pirate a VN that you can somehow legally pay for, well, good luck, and it's probably going to turn out fine. But I won't help you, and I hope you get a virus along with your torrent 

Comments in-line

Litania: I spend my nights shaking my butt (dancing) in front of drunkards, you know? Is something on your mind?
Seeing as the first sentence and second have little to do with each other, I'm guessing it has something to do with the line previous.
Caprese: Why is it you barmaids (? women working at bars? Woman in bars? Not sure what the correct equivalent here is.) are so unreserved/frank/blunt talking about these things?
Litania: Are we? You might feel a little better just by talking about it, and besides, don't you know that acting despondent in front of others is like sending a sign that you want them to care?

Comments in-line

Litania: I spend my nights shaking my butt (dancing) in front of drunkards, you know? Is something on your mind?
Seeing as the first sentence and second have little to do with each other, I'm guessing it has something to do with the line previous.
Caprese: Why is it you barmaids (? women working at bars? Woman in bars? Not sure what the correct equivalent here is.) are so unreserved/frank/blunt talking about these things?
Litania: Are we? You might feel a little better just by talking about it, and besides, don't you know that acting despondent in front of others is like sending a sign that you want them to care?

Heh. This is nothing.
This simply pales in comparison to Pregnant Boys.
Step up the game, boys.

Boukyaku no Rakuen
Due to neglect, the protag starts "talking" to plants, and is sent to a remote academy that doubles as a mental institution for children who are "psychologically challenged". He becomes the only member of the Gardening Club and is effectively given complete control over the academy's extensive gardens. Over time, he comes into contact with other students and/or faculty who all have their own problems, to which he provides relief in the form of illegally-cultivated opium. Will he be able to provide the relief they seek, or will his relationships devolve into addiction-driven exploitation?
Homeroom Teacher
A cheerful woman who serves as the protag's homeroom teacher and Gardening Club's advisor, but has Dependent Personality Disorder. She often wastes class time talking about how lovey-dovey she is with her lover, who lives in the city. As time goes on, however, she talks less and less about him. Eventually, she finds out that he had been cheating on her, at which point he breaks up with her. During this period of time, she starts acting more and more nervous, and finally suffers a nervous breakdown. Protag provides some opium to help her back on her feet. Over time, however, she becomes addicted. Choose:Take advantage of her dependence
Protag starts demanding sexual favors from her in exchange for the opium. As her dependence grows stronger, protag's demands also grow increasingly violent.One day, he finds her dead in her room, having overdosed. Protag leaves the academy and never comes back. BAD END You can't give her any more of the stuff
Protag decides it's best to cut back on the stuff. He starts taking care of her, helping her through withdrawal. She starts developing feelings for him out of gratitude, but fears that it's from her dependent personality disorder, which they work out together. Choose:You convince her that you'll always be there for her.A few years later, she still works as a teacher at the academy. The protag, after graduating, became officially employed as a gardener at the academy. They live together happily. GOOD END You fail to convince herShe starts suffering nervous breakdowns again, and protag has no choice but to provide opium to ease them. Her addiction relapses. One day, protag finds her dead in her room, having overdosed. Protag buries her under a newly-planted cherry tree in the gardens. After graduation, he becomes officially employed as a gardener at the academy. There, he spends the rest of his days caring for the cherry tree. After his death, he is buried under the same tree according to his will. END Other heroines?  
Sources of inspiration:
Under the Cherry Tree by Watanabe Junichi
Norwegian Woods by Murakami Haruki
Le Fruit de la Grisaia by Frontwing