Just putting together a rough storyline.
2000- Twilight and Butterscotch are sent to Frostlost
2001- Guard is formed, Twilight self-elected leader.
2003- major crime is cleaned up
2004- Future guard formed to prevent crimes.
2005- Lily Blossom, daughter of Butterscotch is born.
2006- Twilight's position of governor is eliminated.
2007- Twilight is arrested for plotting to overthrow the guard
2008- Twilight is sentenced to an immortal life in prison.
2009- Twilight's punishment is undone in place of execution.
2010- Frostlost is divided into districts.
2011- Children begin getting recruited into guard training
2012- Riot in shop district leads to mass execution.
2013- Butterscotch is murdered by Snowflake, an escaped convict.
2014- Guard is divided into classes
2015- Liquor is banned from frostlost
2016- over twenty secret alcohol developing facilities found and destroyed.

That's as much as I can come up with right now, add to it. We are trying to get to the date 2100

How am I supposed to have a town drunk when the alcohol facilities are destroyed? I'm leaving this collab. Jk can I make my story prior to the destruction of these facilities?

543188 of course you can, there's time before that date, correct? Your drunk can even be the reason why they are closed down if you want.

Here are just a few ideas:

2017- A clean up of the streets as orphans are gathered up and the homeless are 'relocated'
2018- The worst winter of Frostlost has the city overdependent on the royal family
2019- Fueled by injustice against the common pony, a mass riot at a hoofball game turns into a violent protest.
2020- Lily is recruited by an underground revolution group, with the intent to wipe Canterlot off the map
2021- Recovering slowly from major setbacks, a new govenor decides to constrain movement in and out of the city by having all movement having to be authenticated by the govenor

543188 You could set up an illegal underground alcohol facility where everypony would go without fear of the guard patrols?

Better yet he's a drunk timeline who lost his tardis because he's drunk and no one really knows who he is so the gaurds try to arrest him and... I'll just stick with a town drunk who is responsible for getting everything shut down

So far my story is set to be in 2020 according to the timeline, progressing on as the story progresses.

The Prologue, as well as Chapters 1 and 2 should be up by Saturday.