Now... TTCC lore is quite an interesting doozy to get into as it's been taking quite a differing approach compared to a fan server like TTR for a popular example when it comes to it's over arching story. Events and characters from TTO are loosely connected by virtue of it being based off it in the first place however with how the story progressed throughout the years, gameplay has been altered and affected. Such as the most notable example, the inclusion of the manager cog boss fights after the v1.3.0 ARG but also content like the original boss cog for lawbot hq, Chief Justice retiring from both the game and in lore to then later be replaced with the permanent CLO/Diane Morsecode. Lately not much has been really shown or talked for upcoming new lore events apart from the retcon/revamping of lore to catch new comers up.
To be quite honest, I feel very mixed over how storytelling and lore has been handled in clash, though I might not be able to say as much coming from a new player as compared to somebody who's been playing TTCC since something like the Break The Law or pre 1.3 update days however discussion about it interests me so I'll just go through my thoughts about any lore significant thing that comes to mind as of rn.
Operation: Break the Law was an in game special event that lasted from October 2019 to July 2020. It was heavily focused on the lawbots ending with a complete redesign of lawbot hq and the replacement of Chief Justice with first The Witness Stand-in and then later (and permanently) the Chief Legal Officer.
Alongside the in game events, special lore related comics (now marked legacy comics due to the recent lore retcon/revamp) were released throughout each phrase of the plan and after it showcasing events like Chief Justice resigning and the toon resistence's efforts against the cogs.
From what I've learnt and "researched" off from various sources, break the law was a rather large event that I feel due to the amount of players present throughout those early days of clash just wasn't able to fully spread it's wings and reach the true potential it could've had/seemed to want to achieve cause of that. An unfortunate thing due to a lot of people not being aware of said events that heavily influence later lore and args that would happen such as the treasure trove arg or the idea explored in clash of cogs being more than just mindless machines devoid of any feeling, which once again is just unfortunate cause apart from certain writing moments present within the game or other media like comics being kinda... mid lets put it lightly, there are legitemately interesting dialouge and ideas presented especially with instances like certain manager boss fights or the apriltoons ottoman exchanges.
I'm gonna go more in depth of my feelings/review of the official storyline comics, atleast the ones that are present on the official site as of right now over here
Of course, at the end of the day, I don't expect there to be serious amount of lore or writing nonetheless for a toontown fanserver. While it's influence Who Framed Roger Rabbit did delve very often into less than pg subjects and you could very easily argue how toontown is a story about fighting capitalism and corporatism, the base game is always intended to just be goofy fun times for kids and I wouldn't mind if there was a mix of the two. Also cause a majority of the staff including the writing department are non-proffesionals/people just doing this for fun.