I can think of a few stories that might interest you op.
Blessed Time
- this time loop functions as follows: mc is given the godly power to turn back time 5 years one every five years, he must manually activate it, he is entirely able to die. First loop he ends up in a horrific massacre and barely saves himself, the next couple are him trying to stop said massacre from happening. There is no "fate" and other gods can muck about, but we still get to see a few different "bad ends"
Mother of Learning
- time loop goes like this: mc gets his soul tied up with the actual time looping character, thus bringing him along for the ride. He can not control it, the goal seems to be to stop an invasion from happening. Excellent drama ensues
In both of these we are given very clear depictions of a "bad ending" though neither one are tied to an outside narrative i.e. otome story transmigration. Both have their strengths and weaknesses in avoiding repeating themselves.
I would probably say that this would be an extremely daunting task that will require a tremendous amount of skill to pull off.
You are essentially banking on readers liking your story enough to read it again but with additional hurdles like:
1-your progress is reset. this is very significant. Your MC might be more knowledgeable, but in terms of plot, you are rewinding all the way to the beginning. A lot of readers would drop it there.
2-your first part and the second part would compete against each other. You need to make the first sufficiently shitty to warrant the necessity of the second. Or people wouldn't care for the redo. And at the same time the more shitty you will make it - the more likely you will gain an audience for said tragedy - who wouldn't care about redo anyway.
3-You are essentially writing fanfiction of the story you wrote in the first half.
4-All exposition that happened in 1st part would need to be dropped or the second would sound sluggish. which would mean you will have to skip a ton of early character interactions and it would quickly turn out into a skip ahead to collect riches.
If you want a time loop with the original timeline I would suggest at most short repeatable loops like MoL where you dont have past and present but a chain of them with plot slowly expanding with each one.
While it might be possible if done right, there is a reason time loops use really small intervalls (often hours or days, not even weeks) and "repeat"-stories use the past life only as motivation like "bandits burned my village and now I want to become strong!".
Readers of loops want to see development and movement and each reset only works, if the next loop has really big differences. That's why you have short loops and everything is different and full of suspense.
Meanwhile, readers of redo-stories want to read about the happy redo and not 50k words about a shitty life that destroys the MC. Likewise most people who like to read "kicking down" stories will hate it if the redo will change things too much toward the better.
So it'll be really hard to write something that makes any of these groups really happy. There'll be people who enjoy such story, but you should be aware, that you don't have a clear target group and the number of people who will read through it might be really small... not a reason to not write it. But something you should keep in mind. A lot of tropes and structures exist for a reason: they work for certain audiences.
Good luck, if you try.
But that's a giant mountain to climb...
So you know those stories where the main character is someone that got to the end of their story and suddenly gets the opportunity for a second chance to make things right? For example: Tsuyokute New Sage, Tales of Demons and Gods, Master Magic Efficiently, and A Returner's Magic Should Be Special
Do you ever think the story should've shown us the original timeline instead of just skip to the end only to thrust us back to the beginning where they can just asspull characters that the main character may know but are completely unknown to the audience and in worse cases place the protagonist in a position where they don't know something would happen despite living through the event beforehand. (In fact we aren't even told what happened originally in such cases at all either so we don't know if the new(?) event was caused by the mc or not.)
Now for the questions I actually want an answer to (the first couple were sort of rhetorical), say I write a story where you follow the main character throughout the entire journey and get to the end only for them to find out they messed up big (whether it was their fault or not) and got the worst possible ending (that is they have already been looping in shorter intervals to mitigate minor conflicts but the overarching conflict is seemingly inevitable.), but the only way to avoid this end is to go back to a beginning, one that is even further in the past than when the story originally started. Would this seem like a spectacular fail (As in you feel the story would suddenly feel like you wasted your own time)? If you were to read it yourself would this cause you to drop the story? And finally does it matter that this route makes the original timeline obsolete as you would be following virtually the same plot once you reach the original start of the story but with a more powerful mc and allies?
(Sorry, I tend to ramble a bit when answering questions, which might be fine if I didn’t have janky grammar.)
Sure, you can start anywhere that makes sense, and as long as the MC doesn’t always use the first timeline as a crutch when making decisions, it should be fine. If they do, it will get old fast, and may seem marry sue-ish.
You expect time travel to change or create new situations, so don’t worry when writing one. Though, if the MC always becomes confused or reacts the same way (or similarly) when it happens it will get old fast. It makes it seem as if the MC has learned nothing.
As for new but old characters, it will create 2d characters if the MC knows the right strings to pull to manipulate them, as well as making them seem like an ass. So, try to avoid having the MC manipulate people, if that is not what you want. For the personalities do not have the MC completely know them. They might think they do, but that would both be creepy to the person in question, and unrealistic. People tend to be fickle, so having them act ‘all according to plan’ can be emersion breaking, especially if the MC doesn’t earn it. Also don’t let the MC describe their personality completely, but let the character show themselves, if that makes sense.
When introducing new character, do not introduce them only to solve a issue the MC is having. (I.E. John randomly, when things were getting tough for him, mentions that he had originally killed a certain necromancer. But, this time around, he knows what they were planning, so he keeps the necromancer alive. The necromancer then appears and solves the issue John was in.)
Second question, if this helps I know a series that does that to some extent, but it only mentions it halfway through so it is a spoiler.
Watch or read Saiki Kusuo no Psy-nan. I believe it solves that issue pretty elegantly….
Anyways, all your issues can be solved, as long as you make sure that what you are doing makes sense in context to your story, if not something has gone wrong.
EXAMPLES: If it feels like there was no reason for a character to do something, something has gone wrong. If MC fails for no reason, then something has gone wrong. If MC redoes life like nothing happened, then something has gone wrong. If MC’s motivation makes no sense, then something has gone wrong.
So create a reason, I.E. MC fails because they were wrong about almost everything, then explain why, but if you pull the explanations from no where, then the MC failed for nothing. Foreshadow a bit.
Bad/Unreasonable motivation means that the character is not written well. You can have strange motivations, if the character makes them work. (I.E. kid tries to find their parents after running from home because of an argument, the second they become lonely. Compared to kid tries to find their extremely abusive parents after running away from home after an argument, the second they become lonely.)
