Our home has 4 computers running Windows 8, no hitches (yet). Three of them were upgrades from Windows 7 to Windows 7, the fourth cam with Windows 8 installed. I'm running Windows 8 on a MacBook Pro, thanks to virtualization software from Parallels. At least with Mac OS X I can make my own Image, although it's not well documented by Apple, and have the Image on a USB stick just in case I ever need it. The other two Windows 7 systems were custom-built PCs for gaming, and they had no issues upgrading to Windows 8.
Before giving up on OpenOffice, make sure you try LibreOffice. It is much better than OpenOffice for compatibility with MS's software. It's not always perfect, but it is generally very close - and has some useful features that are missing in MS Office.
As for other software - I could not do my work without a Windows machine, but equally I could not do my work without a Linux machine. And a lot of what I do can work on either platform - but generally much better on Linux.
Too much of my work relies on Office and OpenOffice does not work well enough especially when dealing with files with changes embedded in them. Also many of the applications I use are not supported on Linux. If this were an option, I would have made the jump a long time ago.
You could try CloneZilla. It's Linux based, it will create or restore an image of your hard disk, and as it boots from the DVD/CD drive on your system, it doesn't matter what state your system is in. www.clonezilla.org
Brian, I use ShadowProtect (by StorageCraft). It can restore to 'bare-metal', or you can even run your backup as a virtual machine on another machine (even if that machine has different hardware features). This came in really handy when I had to send in my laptop for repair after a lightning strike.
It uses 'shadowing' to maintain the backup, so it is very non-intrusive to use the computer while backup is in progress. Mine does incremental backup every hour, and full backup once a week. I forget it's even there.
I should mention... I'm not running Windows 8, but they claim Windows 8 support.