Moving to Windows 8: Should you upgrade, or should you do a clean install?

If you’ve been seriously considering taking the plunge and moving to Windows 8, you’ve probably also been wondering whether you should do a clean install or an upgrade. Conventional wisdom says that a clean install gives you the best way to have a solid, running Windows installation. But if you’re like me and have dozens of applications installed, the idea of re-installing all of them can itself be a daunting roadblock. If you’re running Windows 7, and don’t need to switch from 32-bit to 64-bit, then an upgrade is a viable option.
Fortunately Microsoft has actually done a very solid job of making the process of upgrading from Windows 7 to Windows 8 pretty painless. I’ve now upgraded my three main working machines — a laptop, a netbook, and a desktop which doubles as a server and HTPC machine. In each case I’m glad I did, and found the process a lot less jarring than the clean install I did on my fourth machine — which required redoing all my settings and reinstalling all my applications.

Run the Upgrade Assistant

Until now, I haven’t been much of a fan of Microsoft’s upgrade wizards. They typically provided long lists of problems with few solutions, and didn’t do a very good job of isolating which problems were critical and which ones were just a friendly heads-up. Fortunately the Windows 8 version is much improved. In each case it gave me a fairly clearly worded list of applications which had updates for Windows 8 available, ones about which it wasn’t sure, and ones it said wouldn’t work or should be uninstalled before upgrading.
In my case the wizard recommended getting updates for several of my applications — which I did — and pointed out that several others would probably not work after the upgrade. None of them were critical, fortunately. For two of the upgrades, I performed the process with Office 2013 Preview installed, and the third with the RTM version of Office 2013 installed. It worked fine either way.

Performing the upgrade: Down the rabbit hole

Set aside a good chunk of time for the upgrade itself. It can easily take hours to do a full in-place upgrade. The good news is that it happens largely automatically. Simply pressing enter a few times is the only part you need to play. However, it can be easy to get frustrated if you take the cheerful status messages and optimistic percentage bars too seriously. Don’t try to make sense of them.
Perhaps in an attempt to dumb down the process, status messages like “Taking care of a few things…” and “Getting Ready…” wander across the screen while percentage-complete figures vary almost arbitrarily from 0% to 100% and back several times. In particular, “Getting Ready…” appeared after more than an hour and several runs from 0% to 100% had already gone by — making me wonder, ready for what? If you can hold your temper — and your sarcasm — until the end of the seemingly interminable Alice-in-Wonderland-like experience provided by the upgrade process, you’ll have a fully upgraded Windows 8 installation.
Frankly, Microsoft should know better. Providing step-by-step status as the update progressed — much as some previous versions of Windows installers have done — with a percentage readout on the total process and on the current step would be a huge improvement. Instead Microsoft has decided to hide all useful information and only provide confusing tidbits. Better that it had blanked the screen and merely had it come back to life when finished. Perhaps a re-run of the Bill Gates and Jerry Seinfeld ad could be shown during the upgrade so that we all know something is happening? I’m all for simplifying, but not stupidifying.
In my case, all my applications, settings, taskbar entries, and Desktop icons were perfectly in place. Office, including Outlook, Adobe Creative Suite, and other applications worked flawlessly after the upgrade. I did have to get a new version of ATI’s Catalyst software in order to run its control panel. Windows Update didn’t know about it, so I had to head to the ATI site to download it.
You’ll also need to decide whether to use a Microsoft cloud-based login, which allows Microsoft to sync your settings between your Windows 8 machines, much like a Google account allows you to do with Chrome.

Using a cloud-based login

I experimented with both a purely local login and one which was tied to my Microsoft Account (the new name for Microsoft Passport, Microsoft Live ID, etc.) In hindsight I prefer the cloud integration option. It didn’t seem to mess up any of local permissions or applications — much to my surprise — and meant that my settings were instantly applied to all of my Windows 8 machines. That meant that as I upgraded additional machines they’d “learn” settings I’d already made on the other machines, so I wouldn’t have to enter them again.
I did run into one instance where the cloud got a little too pushy. Microsoft remembers where you place the taskbar when you move it around. I like having it on the bottom of my desktop, and on the left on my laptop. However, each time I moved it on one machine it would move itself to match on the others. This was sort of fun the first time, but I quickly learned I needed to search for sync your settings in Windows settings and turn off Desktop personalization if I wanted each system to have its own taskbar orientation.