Greg Broiles may call himself a fuddy-duddy (he’s relucant to upgrade from Windows XP), but he’s got some seriously good advice for anyone looking to upgrade Windows:

Always start with a fresh, complete installation on an empty partition or hard disk.

The easiest way to do this is to just buy a new computer with the new OS already installed; you can use both of them in parallel until you’ve got the new one working correctly …

The second easiest way to do this is to buy a new hard disk; take the old hard disk out of your computer and put it somewhere safe. Install the new hard disk, and then install the new OS on the new hard disk as if you’d just bought a new computer.

The third easiest way to do this is to make a complete image backup of your hard disk(s) using something like Clonezilla or Norton Ghost or Acronis True Image.

Seriously, don’t “upgrade” an existing system – best case, you’ll have a working system that’s got a filesystem full of outdated files that just take up space and confuse you (or the computer). Worst case, you don’t have a working system, and will have to restore from the backup you probably didn’t make because nobody ever told you that upgrading is evil.

Greg is 100% correct. Although I don’t follow his advice. Instead, I make sure I have a current backup (I usually have several) of my files, then plow ahead with the upgrade. If it fails, I’ll be up all night reinstalling the operating system and all my software from scratch, then restoring my files. But at least I know I will have a clean install. And for me, it’s just two computers.