>Do I need to backup everything, and reinstall ALLLLLLLLLLL of my software?

IIRC, Microsoft will not allow you to upgrade to Windows 2000 from Windows ME. However, with Windows XP it is possible.

One alternative is to create a dual boot--one for Windows ME and one for Windows 2000/XP. I use Partition Magic from:

http://www.powerquest.com/

Also, I buy all my OS licenses from:

http://www.monarchcomputer.com/

They are full OEM versions that you can purchase for under $160.00 American.

--Paul