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Keith, I'm almost sure you haven't done what you just suggested (adding 20+ icons to several monitors, in desired order).
Otherwise, you yourself would have added this functionality long time ago, with top priority to your change list!
Hi, +1 for adding this strangely missing feature.
I just tried the workaround and it's not to bad as long has you have the option "All taskbars show all windows." before starting :
- be sure to have the "All taskbars show all windows." setting on.
- on your main taskbar start each program from left to right (wait for each program icon to display on extra monitors). when all programs are launched on each extra monitor pin everything.
In such way it is not too painfull to keep correct order and no need to move any window across monitors.