Your comments

Actually, it doesn't seem to have anything to do with the size of the project. I'm seeing this all the time now. Even after quit and re-open ST2, and open a small project. Rename a file, delete a file, add a file, none of it updates the sidebar.

I've noticed this often lately, too. I think it might happen when you have a large project open with a lot of files to keep track of? The only way I can fix it seems to be quit and restart ST2.

Perhaps in the meantime, a help page accessible from the help menu that listed just the default keyboard shortcuts for menu items (missing or not)? This would make it easier to learn at least the basics than trying to read the entire keymap file, and could explain why some menu options don't display keyboard shortcuts even though they exist.

But it can't be toggled with an existing selection. There is also not one way to do column select, but two depending on whether or not you are using the mouse. Column select with the keyboard using Ctrl-Shift is not a true column/block select mode. It's more like multi-line multi-select. It behaves strangely when you reach the end of the last line (it wraps to a new line). Continuing to hold Ctrl while making your selection results in the selection for each row being dependent on the content on each row, rather than a proper column or block select mode, as the cursor skips by word or tab etc., instead of by column.

These issues could be worked around by making a regular selection from the start to the end point, and converting the selection to column mode.

Alternatively, column or block select mode should work the same for keyboard as it does for mouse. Opt-Click or Shift-Opt and cursor keys should trigger column/block select mode, and moving the selection from the start point should be based on the position of the end point and not the content on every row within the selection.