I have Windows 2000 professional distributed through my company, but I could
not find the proper place to post questions for that version.  I think this
is probably a general Windows issue anyway, so....

I have a scheduled task set up to run the following every weekday morning at
9am:
NET SEND MYPCNAME "Don't forget to run the Daily Report"

It works great as long as I don't ever turn my PC off.  If I turn it off,
say for the weekend, the task will not run on Monday (even if the computer is
back on before 9am) and the task status says "Could not start".

I know that you may be asking, "Why not just do an Outlook reminder?", but
my company uses Groupwise, not Outlook.