It is incredibly difficult to use the timeline feature if the dates are anything outside of a few months apart. I have tried and messed up countless times to set a timeline from 1/1/24 - 1/1/26 (would be so easy if I could type it in to enter) but because of how the timeline column functions, every time I switch years, it loses the first date chosen. Is this why everyone is using date and time formulas instead of the timeline column? The regular date column is easy enough to use, can this not be utilized the same way?
Hi @gillian 
Welcome to the Community!
Have you considered the ‘Start + End = Timeline’ app in the marketplace?
It will auto set the timeline column for you based on two individual date columns holding your start and end dates respectively.
Then you can do it all with automation 
Let me know if you get stuck!
Peta | Upstream Tech
peta@upstreamtech.io
+613 9067 5611
Chat with Peta
Hey @gillian
We’re revamping the timeline column and we want your help!
My name is Amber and I am part of the team responsible for all the columns you see on your monday Boards We’re looking for highly engaged users to shape the future of our timeline column! As a design partner in this journey, you’ll collaborate closely with our product and design teams over the next few weeks and then get early access to the functionality that you helped design!
We’re looking for dedicated users who are excited to provide feedback and work with us to bring this vision to life. If this sounds like you, please fill out this form