Consideration Sure; however classic shell doesn't actually replace the windows shell
![Razz :P](images/smilies/icon_razz.gif)
it just augments it. so having total control can be tricky at times. I dont actually know how difficult it would be, Im just stating that a solution is already available, in a piece of
compatible freeware.. too much modification to the taskbar might break compatibility in unexpected ways.. Though Classic shell has been moving towards the taskbar in the last few updates (with a customizable skin and transparency), Those features were likely checked, and/or modified for compatibility with 7+
Also my suggestion to start with taskscheduler probably wont work; however this should:
http://answers.microsoft.com/en-us/windows/forum/windows_7-desktop/how-to-start-program-before-user-logon-windows-7/2bff97c4-c037-437c-9fa7-b143a3ae5189?auth=1