Put simply, I don’t upgrade operating systems. Ever.

I install any OS new and recommend the same to anyone else. It doesn’t matter if it’s Windows, OS X or Linux. Don’t upgrade. Back up your stuff, wipe the drive and start from scratch with the new OS.

To note, I don’t do this with incremental updates (e.g. XP Service Pack 2 to 3) but rather with significant version changes (e.g. Ubuntu 7 to 8).

In my personal experience, my OS upgrades have consisted mainly with Linux and Windows boxes; neither of them know how to do major version updates correctly and never have.

With Linux, I will encounter some type of upgrade issue without fail. If it’s not X that screws up, it’s the network connection. Or maybe Samba decides to drop all the network shares. Or maybe some other service just magically decided to stop working and absolutely will not work again no matter how many configuration files you manually edit or services you stop/restart or reboots you perform. Or maybe the OS won’t load properly at all. But when you install fresh, ta-da… everything works like it’s supposed to and you can go on your merry way.

With Windows, any OS upgrade will leave an enormous amount of crap left behind by the previous version – always. The drivers that used to work in the old OS will try to load in the new one and BZZT… sorry Charlie, that doesn’t work anymore. In addition, the computer runs slow because it’s got all the preexisting crapola it’s still trying (and failing) to use. But when you install fresh, there’s no crap Windows has to deal with and therefore runs better.

I have never recommended that anyone take an existing OS and install an upgrade on top of it, and I never will.

Most of you out there will be upgrading to Windows 7 from XP when it comes to market. What I suggest you do now is the following:

Take inventory of your software

For every app you use, open up a spreadsheet app like Excel or Calc or Google Docs and list them all there. Include your downloaded stuff, your games and everything else. Consider it to be your own personal how-to guide to “build” your OS the way you like it.

For the downloaded apps in particular, make a separate column with the download link so you don’t have to go hunting for it later.

Keep this spreadsheet up-to-date.

For those that would ask why this is even necessary, the answer is that it’s easier to read a spreadsheet than it is to fumble thru a huge list of files and folders. Also, there’s probably at least a few apps you have to install in a specific order. Having the inventory on spreadsheet makes that easy to follow.

(For Linux users I also recommend doing the software inventory spreadsheet. Note the apps you have installed from your respective repositories. Just because you use Linux doesn’t mean you don’t take inventory of what’s on your box.)

Burn any/all downloaded app(s) to CD or DVD or copy to USB stick

CDs and DVDs are cheap and readily available. Buy a 50-pack of a decent brand (one can never have too many) and a set of fine point Sharpie markers. Set aside some time to burn all your stuff.

Recommendation: I suggest burning each disc twice just in case the first one fails or an optical drive decides “I don’t want to play nice with this disc” and scratches it all up.

Alternative: Use a large-capacity USB stick. 16GB versions start at 25 bucks. And it’s most likely true that all your downloaded app-installer files don’t get anywhere near that capacity when combined.

Need more space? Get a 32GB stick. Still need more? Get a 64GB.

Before you wince at the price of the 64’s, bear in mind this is a little USB stick we’re talking about.

If you can fit all your app installer files on a single USB stick, trust me when I say that’s darned convenient. Having all your must-have apps on a single stick is so much easier to deal with compared to flipping thru disc after disc.

Why don’t I recommend external hard drives?

Because you’re most likely using it as a primary backup for other things besides downloaded apps, and you’re probably using it routinely. When doing an app-inventory backup, it’s best use a store-and-forget method until you need it. Discs and USB sticks allow you to do that.

Collect any/all from-OEM discs, put them all together and categorize

These are CDs supplied with your printer, digital camera, camcorder, digital dictation device, GPS, etc. Buy a disc folder or box and stuff ‘em all in there. The software is probably more important to you than the manuals so you might as well keep it all together.

I’m not saying to throw out the boxes or manuals – but put the discs together.

If you don’t feel like doing that, burn copies of the driver/software discs and do it that way.

If you do this stuff now, it will make your new-OS install a whole lot simpler in the future

Most people do the above the day they buy a new OS. Wrong. Don’t do that. Doing it all in a day means you’re guaranteed to miss something along the way. That OEM driver disc you thought you had will end up missing. That file you thought you had won’t be there or backed up anywhere.

And let’s say that you don’t plan on jumping to Windows 7 the week it’s released. That’s fine – but you should still do inventory and back up your apps regardless. There is never such a thing as being too prepared when it comes to computers and operating systems.