What type of character should I write about first in a potential series of books?
I have a world in which many characters live in. At first, I thought they all could be part of one novel (kind of like Sherwood Anderson's book Winesburg, Ohio or the movie Short Cuts (1993) by Robert Altman), perhaps even a trilogy. But more thought into all of these characters leads me to believe a series could be appropriate (think Terry Pratchett's Discworld novels), perhaps separate books focusing mainly on one character each.
This is pretty much a monumental task, which I'm ok with, but what type of character would be good to start a series with? Not all characters would necessarily cross paths either, so perhaps 2-3 could be in the same book, and perhaps some could be in multiple books as well switching between MC and secondary character.
To clarify the question, what would be the best way to set the tone for this series, like something to introduce the world. Or should I just let the world gradually become more detailed with every book, like a gradual spilling of information about the world.
Does it really matter what type of character to start a series with?
I'm aware this could be too open of a discussion, but if there are any literary dos and don'ts about series starting that I'm not aware of, or perhaps stronger, and proven, ways to be more effective in the beginning, I would greatly appreciate those elements included in the answers.
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Does it really matter what type of character to start a series with?
Most of the time: Yes.
A lot of longer series have an overarching storyline. I am thinking about Black Dagger for example because the (English) books switch their point of view with every book (as fas as I know; the German ones switch every three books, but I have been told the German ones are basically just the English ones broken into multiple parts).
Basically that series had a group of people doing stuff. They've been doing stuff for quite some time without a lot of action (well, without any difference in the kind of action) happening. And then someone from the outside joined - which is the first character that is used as a main character for a book. This is the point where things start to get into motion. Where new stuff happens. Where new characters start joining over the course of weeks/months/years.
If you want an overarching plot where all the different characters have little stories for themselves you should think about when things start to go from "(relatively) ordinary stuff happens" to "weird/crazy/unusual/dangerous/... stuff happens" and especially which character is somehow tangled up the most in this - for example by thinking about who the first contact with something is. That is your starting character.
Another story with different characters is the "Otherworld" series. There are three sisters. The first book is about "The Witch", the second about "The Cat" and the third about "The Vampire". Then the fourth is from the perspective of the witch again, the fifth from the cat, ...
In this case every character has their own story and their own things to do, but they regularly meet each other. They spend a lot of time together, but the other two don't have so important stuff happening to them personally. The focus is on one of them in each book, even if the overall stuff happening is happening to all of them, possibly at the same time.
Conclusion: The overarching story is what defines which character's turn it should be.
If you want every person to be completely different and independent from each other, except for a few very rare occasion compared to the amount of books you want to write (and that would need to be a lot) then you can go and read the above statement again, in a different light: the events of the time define who's turn it is. You will want to make sure that the reader knows when something happens in comparison to what other books already tell. Therefore you will want to make sure that certain events can be observed from different books and that may give you a timeline you can use to decide which character is influenced the most by an event - which again is your character for the book.
Other than that I would make sure that the first character is very likeable - you want to make sure that people pick up that book, get a feeling for your style and want to read the next one. After a couple of books they will know that each one can be different and they will expect this, allowing you to experiment a bit more - don't take too many risks with the first one.
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I suggest you start with an Innocent (or an Outsider) — a Cabbagehead kind of character, someone who doesn't know anything about your world so the world has to be explained to and/or experienced by this character.
This gives you an easy path to explain things about your world to the reader, because everything is also being explained to the character. Once you've given your reader an on-ramp to your created world, bringing in other characters who are more complex, crazier, higher up in politics, etc. to star in other books is much easier, because you aren't trying to explain the world at the same time.
As an example: Mercedes Lackey has written like 50 books in her Valdemar series, around different characters, set in many different times and cultures. The first trilogy was about a 13YO peasant girl who is selected to become part of the main kingdom's magical police force, the Heralds. Through her literal schooling and training, she learns about the kingdom, magic, history, culture, society, and neighboring countries. From there, Lackey had the freedom to add on other characters and countries as she saw fit in future books. Some stories are set over a thousand years before her original trilogy; some are set thousands of miles away and barely interact with the main kingdom if at all.
Outsider/Isolated Child Who Becomes Chosen One is a classic opener: the Belgariad, Harry Potter, A Wrinkle in Time, The Dark Is Rising, The Wizard of Oz, Menolly from Anne McCaffrey's Harper Hall series, I'm sure you can think of more. Having other wiser characters teach your Chosen One about the world not only lets you do world-building in a way which is relevant to the plot, it opens up lots of places to introduce other characters/settings/nations/cultures/etc. who can then be the focus of future stories.
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Start by writing about a character into whom you have the most insight, about whom you have the most to say. Art is about vision. It is about seeing what others do not see and transforming it into words so that they can see it.
This is not as highfalutin as it may sound. A character becomes compelling, becomes worth devoting our time to as readers, insofar as we recognize them as human. The foundation of great storytelling it to create characters who read human, and who continue to read as human when put under pressure. This is true from the merest potboiler to the most profound work of literature. Human recognizes human.
If you can write a character that reads as human, that continue to read as human when you put them under stress, and that undergoes a recognizable story arc, you will have a salable story. The best character to start with it the one you best understand.
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