Man, this is one topic that took me a while to get to.
I for one think that depending on the type of story you want to tell, chronology can either be very simple, or extremely complex. On the simple side, a self contained story does not need to have much in terms of background and world building in general. If I write a self-contained story, I want it to be simple and to the point, and the characters and settings will establish the timeline of events. Then again, as I've publicited to no end, I have a "TrappVerse" which main focus is the current era, starting from 2019 to 2023 at the moment, but I have thought of a few characters moving past that time frame. To put things in perspective, here's how I picture my timeline for all my comics:
Sex Tales issues 1 and 2 basically occur in tandem in 2019, shortly before the canonical event that was the COVID pandemic. Also in 2019, the Ecchi Squad meetup with Marco Torres occurs. Sex Tales 3 and 4 occur in 2020, with Emi Akatsuki about to graduate high school and awakening as a succubus. Starting with Sex Tales 5, we move into 2022, year where Black Trapper Media LLC, the company under which BTM Babes operates, was founded by Marco. Mid to late 2022 is also the year where Hikaru Ichinose is hired by Sigma Idol Agency and the Gravure Love storyline begins and where the story for VG Elf would start. CNC Baby would start at around January of 2023 as well, happening in tandem with the mainline stories for VG Elf, Gravure Love and The Goddess's Journal. But those are just my approximations.
As a writer, it is very easy to diverge into different time periods and establish multiple characters... But it is also very easy to lose track of the story you want to tell. Giving more emphasis to the world around the characters can very easily work against them and the overarching plot involving them. And chronology is a tool that can very easily break your story if you don't plan it properly and have your characters set from the get-go before writing.
If I write a story, I want it to be set at a specific time. Problem is, if I don't put my mind and time to it (which has proven to be next to impossible lately...), then the substance in the story fades away.