Why not find a way to automate this,

Why not find a way to automate every single change that the vscode team makes that may break something?

Or why not let users do whatever?

Ultimately, users can do whatever.

But when they need help, they come to me.

I have a recommended list of settings for things that should already be defaults, to guide them away from footguns, and to prevent themselves from needing my help in the first place. But I also sometimes need to go around with a critical (usually temporary) list of changes for when a vscode update truly borks something up.

My concern was potentially needing to go around the office once a month for those critical fixes to once a week.

This is why I suggested multiple release channels. Have a weekly release for developers who are okay with the trade-off of more frequently broken setups for newer features faster, and have a monthly release for developers who want more stable environments.

It'd be a lot easier for me to run the weekly channel to be kept abreast of any changes, and I can support other coworkers on a monthly cycle.