unfortunately, i don't actually really have any concrete ideas, though. i'll share the thoughts i did have below in case they help springboard anyone else to a more useful conclusion.
scientifically, winter is defined as being from about December 20th to March 20th. rest in peace Mx. Hakobyan for being born on the 19th and therefore just barely not qualifying. if "the first of solitary winter nights" is referring to a specific character via their birthday, i think it would be one of these three:
Teruko (born January 7th). this date is pretty early into the winter, and it's easy to imagine Teruko being solitary at this time.
Mai (born February 1st). earns bonus points for being born on the first, imo.
MonoTV (birthday listed as January 0th). ??? it's really close to 1/1, which would be double "first."
Eden is also born in this winter time frame (December 31st), but given that New Year's Eve is a holiday and Eden is a very friendly person, i find it difficult to imagine that she would be "lonely" on that night.
this tweet could also be a subtle way of referring to an episode by its release date. Prologue Episode 1 has the same release date as Mai's birthday, which means it also falls in the winter timeframe (February 1st). the rest of the Prologue was released day-by-day afterward, and therefore also in winter, but i struggle to see how any of them hold a candle to the first episode, released on the 1st.
Chapter 1 Episode 1 also debuted in winter (January 22). the entire rest of the chapter followed within winter 2021.
Chapter 2 Part 1 also had a winter debut (January 27), though only Episodes 1-8 came out in winter. none of Chapter 2 Part 2 came out during the winter.
in terms of MVs, being on the series' anniversary, Fool's Table joins the Mai-coded February 1st group. Yoidoreshirazu also came out on March 3rd, which technically falls within our winter range, but... really?
due to how many possible winter episodes there are, i really think this is a dead end. if anyone does want to investigate this thread further, i'd wager your odds are best looking at Prologue Episode 1.
alternatively, this could be a teaser for an episode which will be released at some point in the future. i'll touch on the upcoming Arei and Ace bonus episodes in just a second, but for now, we're going to stick to strictly dates in our world.
i don't think that December 20th or January 1st or whatever would be the release date of the bonus episodes because 1) they already seem pretty close to complete(!!!) and 2) saying that you're going to release bonus episodes 6 months early seems a little... strange? but maybe i just don't understand DRDTdev's game.
hypothetically, this could also be a clue that chapter 3 will begin this winter, on a lonely night. however, i think this is unlikely in the opposite direction-- as far as i can gauge, Chapter 3 is probably not close enough to complete to be ready for viewer consumption this winter. maybe if it were close to the end of the range, i.e. in March. announcing a full chapter release 6-9 months early would be understandable, except that it's so far in the future that, at least if it were me, i wouldn't be certain of how much work i'd be able to get done within that time frame.
while none of the main cast appears to have names meaning winter, there is one side character who does: Arei's older sister, Fuyuko. Her and Natsuko have seasonal-themed names, with the character used for "fuyu" meaning "winter," and the character used for "natsu" meaning "summer" in Japanese. hence, maybe this tweet is being used to foreshadow that Natsuko will be alone?
this option seems dubious to me just because i doubt we will be getting too much Fuyuko content moving forward. like, hypothetically, we could get a "one of the evil stepsisters is good"-type plot in Arei's bonus episode, but that seems pretty tangential to the story as a whole.
this is the option that really seems the most likely. gleamingtempest already discussed this idea, but this tweet may very likely be foreshadowing Ace's bonus episode, and how he's now lonely after his friend (Taylor) died.
i wanted to expand upon gleamingtempest's point by once again questioning the timing of Taylor's death. if Ace's bonus episode is the first of lonely nights, it seems like Taylor's death must've been pretty recent, right? like, the bonus episode takes place during the first winter that Ace has spent alone.
if we assume that Ace, like Xander and Min, will be talking with Mai during his bonus episode, we can extrapolate that either A) the first winter Ace spent at Hope's Peak was the first winter after Taylor's passing, or B) Mai knew Ace prior to their admittance to Hope's Peak.
i could really see it either way, given that (from the teasers we've seen), Arei possibly appears to be a child during her scene? which could suggest that Mai had known Arei since childhood. or, alternatively, these two facts may suggest that Mai will not be featuring in Ace and Arei's bonus episodes; perhaps a relationship with Mai was a shared theme that Xander and Min's episodes shared while Arei's and Ace's will, like, both take place during their childhoods.
at any rate, i'm hopeful that we may get answers to this question quite soon! standard disclaimer that, of course, DRDTdev can take as long as they damn well please to do the favor of continuing the story for us, but it really seems like the bonus episodes may be almost done. and in that case, i'm super excited to see the story continue!
hopefully it was okay to ramble on your post like this, skulemojee 😅