I’ve now installed Windows 8 five times. Some installations have gone amazingly well, and one went horribly awry, bricking an entire PC. Having experienced the best and worst Windows 8 has to offer, let provide some recommendations on how to upgrade with the least pain possible.

.0 products

Windows 8 is what we call a “.0” product, the first in what will be a new series. The last time Apple did a .0 product was the move to OS X, which is why recent upgrades seem to be relatively painless. Microsoft makes major changes far more often, generally to address critical security holes and to catch up with leaps forward in hardware.

Microsoft’s past .0 products have included Vista, Windows 2000, and Windows 95; all came with plenty of teething pains. Having experienced all of those (I once bricked my CEO’s laptop with Windows 95 accidentally) my standard recommendation is to not upgrade early to any .0 product unless you are willing to experience some pain.

Having said that, Windows 8 has generally performed far better than any .0 product I’ve so far experienced but, for most thinking about upgrading existing hardware, I’d recommend waiting at least a quarter so most of the hardware incompatibilities and other issues have been corrected.

The best path early on is to simply buy something that already is running the OS, because it has been tested at several levels. To date, every Windows 8 machine I’ve been sent has performed flawlessly.

Bricking a PC

The worst experience I had was with a very high-end, very unique PC that Intel had sent over to showcase extreme performance. I figured if Windows 8 would upgrade this machine, it could upgrade any machine. Turns out it can’t.

The upgrade seemed to work, but I noticed that the one of the USB systems was constantly failing and resetting, so clearly the system didn’t like one of the drivers. I started to perform a clean installation (deleting the partitions and loading the system fresh), but that resulted in blue screens of death and the installation wouldn’t complete.

Lesson learned: With a very highly customized system, there is a risk right now that Windows 8 won’t complete installation. The fix will be to swap out the motherboard with one that is Windows 8 certified, and the problem will clear. If you want to try anyway, make sure you take a full system image copy of your drive so you can restore it back to the way it was if Windows 8 doesn’t work. Because I hadn’t done that, I didn’t have this option.

Wrecking a laptop

Windows 8 uses the edges of the screen (or a touchscreen) to bring up menus. Many laptops that shipped before Windows 8 (if not most) have raised edges around the pad as a design feature, or are “center weighted” to prevent accidentally moving the cursor while you type. Both these features work poorly with Windows 8. Finally, multi-touch touchpads are still rare, and Windows 8 without a good touchpad sucks in use. You can use a mouse, it’s far from ideal. Products like this are better off left running Windows 7.

Upgrading versus installing from scratch

Generally, I advise a clean installation. It cleans out your PC of all the crap that you’ve loaded, both on purpose and accidentally from malware (unless you have installed a root kit). While it takes longer, the end result is much closer to a brand new system. However, you have to reinstall all of your apps. An upgrade leaves in place all of your apps, and Windows 8 has the best upgrade process I’ve ever seen from Microsoft.

That said, I think it is even more important to do a clean installation with Windows 8. This is because if you choose to install new apps from the Windows Store going forward, you can easily migrate these apps and get the benefits of clean installation, plus the speed of an “in place” upgrade. Going from Windows 8 to Windows 9, 10 and so on will go much more easily if you make a clean break from Windows 7 and embrace Windows 8 apps. The exception, ironically, is Microsoft Office, which won’t fit this model until the Windows 9 timeframe.

On my last system, I put together the hardware, installed Windows 8 and Office, and was in full production in under two hours. That’s going from a bare case and parts, all in separate boxes, to an up and running PC on my desk. I’m convinced that if I didn’t screw around (I had some issues with a cheap power supply I had to address), I could do it in under an hour. Historically it takes me around four hours to do the same thing, and even then, all my settings and files aren’t fully in place for several days.

Acquiring the OS

While the installation may be simpler, choosing a package to install is more confusing this year. If you buy an upgrade package, you get Windows 8 Pro, if you install on fresh hardware or you are buying a new PC, chances are it comes with plain Windows 8. (Personally, I have yet to miss any of the features that are uniquely in Pro.) Even more confusing: If you upgrade Windows 8 to Pro, you get Media Center, but if you upgrade to Pro or put Pro on a new system, you don’t. If you download the Windows 8 Pro upgrade from Microsoft, it costs around $40; if you buy the DVD it costs around $65; if you buy the “systems builder” copy of Windows 8 it costs around $85; if you buy the “system builder” copy of Windows 8 Pro you are approaching $125. Windows Media Center is around $10 on top of Pro, and the upgrade from Windows 8 to Pro is $65.

The cheapest path if you have a Windows 7 system (along with the image disk) is to download and install the Windows 8 Pro upgrade for $40, and then upgrade it to Media Center for another $10 (assuming you want Media Center). The most expensive way is to buy the system builder Windows 8 for around $85, then buy the upgrade to Pro for $65 on DVD. This lands you the same result for around $150, or about $100 more, for the convenience of not having to track down your Windows 7 DVD.

Wrapping up

I’ve completely moved over to Windows 8. I’m using Surface while on the road, and Windows 8 Pro on my two primary desktops. If you are happy with Windows 7, I’d stay there until you have a compelling reason to move or need to buy new hardware. The easiest long-term upgrade will be simply buying hardware designed for Windows 8 when you’re ready. If you do want to upgrade existing hardware, you’re best off waiting until after the new year to execute the move. Most of the fixes from us early adopters will be in the product by then, and help resources will be far less stressed out if you need to use them.

One thing to keep in mind, though: That $40 download price for the upgrade is supposed to expire, so you may want to get it and the key while it is on sale, then do the upgrade when ready.

Good luck! If you’ve made the move to Windows 8 already – or tried and bounced – I’d love to see your comments on the experience. For me, even with all the .0 warts, this has been the easiest and fastest OS I’ve ever installed. It’s fun to build systems again… at least as long as you build them using a motherboard that was designed for Windows 8.