Very open to feedback, because canon is as spread out as Muzan after his first date with Sun Breathing. Instead of tracking the year or distance from the current timeline, we shall track this by Shinobu's age (roughly, in most spots). Despite being centered around Shinobu's life events, I'm also diving into Aoi's life, the other Pillars' timelines of life events too, and doing some conjecture about Shinobu's deceased Tsuguko. Should be obvious, but spoilers ahead. Childhood: Raised by kind parents who possessed medical knowledge. Sometime around elementary school age (at the oldest, I'd put her at 11, but probably younger), parents are killed by a demon, house is demolished, and she and Kanae are rescued by Himejima (who was maybe around 20 or younger at the time), who hands them off to the Kakushi. Training under cultivators usually takes about a year. She and Kanae perhaps passed the Final Selection when Shinobu was around 12-ish, give or take. Whether Kanae becomes a Pillar first or they establish the hospital at the Butterfly Mansion first is unclear, but these events happen relatively quickly. I suspect they might have had access to a lot of savings from their parents. Furthermore, this makes Kanae one of the many Pillars in the recent generation who blows that "it usually takes five years to become a Pillar" Taisho Secret away.
Sometime after Kanae becomes a Pillar, Sanemi becomes a Pillar. Giyuu was a Pillar before Sanemi was; the three of them were the same age. 17 when they would have had chances to interact. For comparison, Giyuu and Sabito were 13 at the time of the Final Selection, so Giyuu would have already been in the Corp longer than Kanae and Shinobu. Kanae is killed by Douma (Shinobu is age 14, one of the only pieces of this timeline we can be certain of). As she wished in her dying moments for Shinobu to live a normal life, she may or may not have had Shinobu as her Tsuguko, or had any Tsuguko at all. Shinobu, age 14, becomes the head of the Butterfly Mansion household, where she already has five adoptive/pseudo younger sisters. At this point she takes on a cheerful personality, as well as probably set her heart on becoming a Pillar as soon as possible and becoming strong enough to defeat the demon that killed Kanae. Aoi's circumstances are important (and curious) because the second fanbook tells us both that she practiced Water Breathing and that she passed the same Final Selection as Muichiro. Since Muichiro became a Pillar two months after taking up the sword, that means he went almost straight from sword to Final Selection to Pillar. We don't know how much recovery time he needed after losing Yuichiro at age 11, because he wasn't among the Pillars in the Rengoku Gaiden, so he perhaps only started practicing the sword closer to late 12 or age 13 (putting Aoi around 14, 15-ish when she passed the Final Selection, and presumably quit the sword right after that).
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It's interesting to note what a different relationship Aoi has with Shinobu than Kanao does, especially since Aoi was there first but Kanao was adopted as a sister in a more all-encompassing sense. Due to whatever circumstances with her Water Breath cultivator (possibly difficulty in housing a lone girl among a bunch of male students), Aoi needed to live elsewhere during her training. The Butterfly Mansion was a good spot, so Kanae and Shinobu agreed, like sponsoring a junior, and in exchange Aoi helped out around the house and hospital. Aoi kept her own last name, as she had her own family to avenge. When Kanao came in, it was purely out of wanting to help an orphan who wound up staying with them instead of being adopted out, which is why she was given a family identity and an opportunity to take the Kochou name if she wanted to (or even Aoi's family name).
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They were probably treated differently because of the nature of how they came in and an assumption that Aoi would leave as soon as she entered the Corp. As Kiyo, Naho, and Sumi came in, it was a weird middle ground of whether they were just looked after until something better for them came along or if they were adopted as sisters as fully as Kanao was. Ultimately, they still retained a lot of their identities from before they were orphaned, and it was more of a pseudo-sisterhood, which Aoi had sort of fallen into as well. But, once Aoi entered the Corp and then quit the sword, she probably didn't feel she could turn to her cultivator for any help, so at that point Shinobu took more full responsibility for her as a permanent household member. Moving back on to Shinobu's timeline, if I'm remembering the Giyuu Gaiden correctly (it's been a while since I read it so I don't recall exactly), that story took place shortly after Giyuu sent Tanjiro and Nezuko to Urokodaki, and it was also shortly after Shinobu became a Pillar. Since Tanjiro took two years to train after that, that would put her at age 16. Since Kanao joined the Corp in the same batch as Tanjiro, that means Shinobu would have had about two years between becoming a Pillar and taking Kanao as her official Tsuguko (I stress 'official' because it comes with distinction Tengen respects, it's not casual "sure, I'll look after you" thing).
In that time, she had (at least) three other previous Tsuguko, all girls given butterfly hairpins, and who were all killed by demons in that two year period. Knowing how likely she is to be killed before she has an opportunity to avenge Kanae, Shinobu was likely in a hurry to train a Tsuguko and started trying to pass her knowledge on right away. It's possible they were even closer in age to her than Kanao, maybe even older, and quite possibly physically stronger. It's possible they were trained under Flower Breathing cultivators and still used that Breath, which would have given Kanao opportunities to learn by watching. That said, Shinobu doesn't mention or think back to her Tsuguko often, and they never appear in Kanao's flashbacks, though their deaths are some of the little pieces that strengthen her resolve to slay demons (she seems to care more about how her pseudo -sisters' families were killed by them). My guess is that Shinobu made a clear divide between family and work, so as to protect the little girls from getting attached to more people who were likely to be taken away from them.
Likely, her Tsuguko and the Butterfly Mansion girls lived in separate spaces and had very little interaction, and their Pillar/Tsuguko relationship was kept very formal so they could all focus on their demon slaying goals (albeit they were probably fond of each other anyway, signified by the butterfly hairpins). Rengoku become a Pillar (around age 18 or 19, and since he was raised practicing Flame Breathing he probably finished the Final Selection around age 12 or 13, so it clearly took him a more normal period of time to become a Pillar. Mitsuri becomes a Pillar (around age 18 or 19-a friend, yay! On these note, please also me to jump backwards a few years to when Kanae was still alive. Uzui had to have been a Pillar by at least age 18, but given the state of Ubuyashiki's illness, probably a lot earlier than that, and he probably didn't take very long to become a Pillar after entering the Corp. Since Giyuu was already a Pillar in Sanemi's flashback, then he attained Pillarhood by, at the very oldest, age 17, so it took him four years or less. Interesting that in all these four or more years he's been convinced the position is vacant, there's no one else who performs Pillar-worthy achievement in the Corp's most widely used Breath style.
But, I suspect Shinobu bonds more readily with girls.
That really drives home the difference between the Pillars and the average cannon fodder. Kanao sneaks out to the Final Selection of her own will and with self-studied Flower Breathing, officially becomes a member of the Corp. Shinobu worries Kanao was just doing this because it's what everyone around her does, as Kanao cannot express that she's built her own hatred for demons. Censuring Kanao a bit for her choice to go against her sisters' wishes and take up the sword, for now she risks death and giving the other pseudo-sisters yet another person to grieve. Given the risky nature of their work, Shinobu feels forced to treat her the same strict way she treated her Tsuguko instead of treat her as a sister. Kanao accepts this and goes from treating Shinobu as her sister to treating her as her master (calling her "Shihan" instead of "Shinobu-neesan"). Over the course of the events of canon, Tanjiro and company spend a very large portion of their time in recovery at the Butterfly Mansion (even if a large portion of that time is spent unconscious), they might as well be pseudo-adoptive little brothers. But, I suspect Shinobu bonds more readily with girls. Also in that time, Kanao speeds up the ranks (she attains Hinoto rank, the 7th of 10 ranks, while Tanjiro & co attain the one above that, Hinoe). Furthermore, thanks to Tanjiro's influence, Kanao also makes leap and bounds in being able to express herself, like something finally broke through.
This at last leaves Shinobu somewhat relieved, after maybe five years or so since she first adopted Kanao. By that time she is getting anxious about the impending final battles (and her death, which she has deemed inevitable but purposeful), and she tells Kanao the plan. And then Oyakata-sama is like, "heeeey, so I heard you want to be friends with demons, I got you one, her name is Tamayo." (It's possible he already told her he was planning to get Tamayo's help and wanted her cooperation, but he didn't actually approach Tamayo about it until after Pillar Training started (though by Kimetsu logic, it's highly possible that the crowd talking to Tamayo took place much earlier than when it was presented). I gotta wonder how quickly they worked to combine their research and if the other girls in the mansion had any idea who Tamayo and Yushiro were. And then, at age 18 (or likely 19 given the progression of the series and very lengthy recovery periods, heck maybe even 20), Douma. Shinobu dies, Kanao switches back to calling her Shinobu-neesan instead of Shihan, Kanae's butterfly hairpin which Kanao wore breaks in battles, Shinobu exacts her revenge on Douma while her efforts against Muzan are also in motion and then she reunites with Kanae and her parents in spirit, and Kanao wears Shinobu's butterfly hairpin in the final showdown and then she makes Shinobu the surprise hero in the surprise final battle to save Tanjiro. It was a really long night, and a really short, busy life.
New World. It constitutes the main territory of one of the Four Emperors, Big Mom, and her crew, the Big Mom Pirates, which extends around Whole Cake Island. It is navigable with a New World Log Pose. According to Pekoms, it is considered one large, powerful nation, and Big Mom as its queen wants it to become a utopia that unifies all races of the world. Totto Land is the general setting for the Whole Cake Island Arc. Totto Land is a massive archipelago with Whole Cake Island, Big Mom's base of operation, in its center, and 34 subsidiary islands, arranged roughly in concentric circles. Each subsidiary island is ruled by a member of the Charlotte Family as its minister. Most islands are themed after food. The territory's border is lined by a weather phenomenon known as "Cotton Candy Snow" (（）, Wata ame Yuki?) (known as Cotton Candy Flurry in the English dub) in which small bits of cotton candy gently descends from the sky. Whole Cake Island: The central and main island, themed after cake. It is the base of operations of the Big Mom Pirates. 100% Island: It is governed by Minister of Juice Smoothie. Biscuits Island: An island themed after biscuits. It is located northwestern to Whole Cake Island. It is the fifth island of the Charlotte Family siblings' secret route to Whole Cake Island. It is governed by Minister of Biscuits Cracker.