Is there a way I can use the middle click or maybe (Ctrl+Alt+Up) to a particular column across all lines in a long fil
In Mac OS X, replace Ctrl with CMD key. So it'll be,
CMD+A - select all. CMD+Shift+L - split selection into lines. Then move all cursors with left/right, select with Shift+left/right. Move all cursors to start of line with Home.