So I'm working on a book (the plan is to make it a series) covering the lives of a bunch of immortals (vampires, werewolves, and other such creatures secretly living among humanity). It starts in 1990, but will gradually advance through the years getting closer and closer to modern day, and a recurring part of the story is how their efforts to stay a secret keep getting harder the more advanced human technology gets. This will play a massive role at the climax of the series as I envision it, though obviously for spoiler reasons I can't say more. My issue is I'm not sure how to handle the passage of time here. Should I have it be like Harry Potter but on a longer timescale, where one book will cover a story arc that takes multiple in-story years to conclude? Should I tell stories that take place on a smaller timescale and skip ahead massive amounts of time between them? Some other method that I can't think of at the moment? I'm having difficulty wrapping my head around the pros and cons of each method, so I was wondering if anyone had any advice on how to decide how to tackle this. If it helps, for context, the story is heavily implied to be the main character writing a sort of memoir of his life and his adventures with his friends years after the fact.
If each timeline has enough to make it into its own book, I'd say go for it. Otherwise, if it's relevant in some way or another, you could do something like: Placename, Year #. Paragraph on (preferably) significant changes (politics, the change in architecture, how characters rode on horseback, but now ride in metal ones). Something to establish the setting before introducing the cast/how these changes affect the story.
Use this device to set up how you want the story to be structured. Since you put it as such, then I recommend structuring each 'arc' of the 'memoir' focused on a specific friend or group, the interlink characters and subplots between each arc. An overarching plot HP-style works if you have some sort of grand plan/device that means something at for the final climax of the story.
i.e. a) Multiple books focused on each main character/group, or b) one main character and multiple memoir chapters as novellas, or c) short stories/novellas from different viewpoints with an interlocking arc. Depends on what you want and how much story you have
Too many breaks in time will create validity issues in continuity of characters. A lot can happen in just a single year, so its better to try in progress the timeline more slowly. You also dont need as many earlier ones. They can be used in the form of flashbacks, or better yet, they can be told as stoties within the main story, to give a folklore sort of feel. These earlier events can simply be used as background, or inferred as well. You dont need to start with a character too early. Mystery and gray area before the events of the story gives interest and tension that straight revealing cant.
So you're saying I should start the story chronologically closer to the end than I expected to, and flash back to earlier to tell some of these other stories I had planned?
It's important to remember that you have existing tools available. An example would be the flashback. I believe the problem you're suffering from is a lack of perspective. You consider a measly few decades to be "a long time" yet to an immortal, it's just as quick as taking a breath or blinking. Time passes very differently for creatures not plagued by the evolutionary failure of aging. The important part is not how you should convey timelines, it's how well you know the events of your story. The more intimate your knowledge is, the more free you are to play with the particulars. Solidify the image of events in your mind and let your gut instinct do the rest. Your gut is always on your side, even if what it asks doesn't seem to make sense. Trust it. It already trusts you.