My take on the best and worst Windows ever

My buddy Ed Bott, who has much better credentials to be doing this sort of thing than I do, has weighed in with his report card on every version of Windows that has been released. In his post, Ed rates each version on a scale from 1 to 10 and provides sound, cogent explanations for why he graded each release as he did. It's a solid exercise in historical review from someone who has had his sleeves rolled up and his arms inserted up to the elbows in figuring out the workings of the world's most widely used operating system for its entire run.

Me? I've been an on-again, off-again journalist and chronicler over the years. I spent a significant portion of Window's early days living in the Macintosh world as a graphic designer, service bureau operator, software and hardware evangelist, radio personality, and magazine columnist. Even during that Mac-heavy period in my life, I  used every version of Windows, was one of the first "Mac guys" in the high-res output business to support files created in applications like CorelDraw and Microsoft Publisher, and have been a passionate advocate of the Tablet PC platform since its inception.

I've gotten over the fan-boy syndrome (quite some time ago thankfully) and feel no need to defend any particular platform, operating system, or company. I like to think I'm a fairly realistic and unaligned observer of the industry while at the same time managing to sustain a high level of enthusiasm for things I think are done well.

Looking at my current slate of gadgets, I think it's hard to argue with this contention. At this very moment, the devices I'm working with on a steady basis include:

• Lenovo ThinkPad X60t Tablet PC running Vista Business
  
• Apple MacBook (white) bumped up to 2GB RAM and a 160GB hard drive
• Palm Treo 700P (Verizon)
• Nokia N93 "handheld multimedia computer" – marketing exuberance notwithstanding, this is way more than a camera phone
• Nokia 770 Internet Tablet (Linux)
• Asus R2H Ultra Mobile PC running Vista Ultimate
• Apple iPod 30GB (5G)

I use all of these devices almost every day and the core tools all day long. I'm equally comfortable (or uncomfortable) working in Vista, Windows XP SP2, Mac OS X, Palm OS, Symbian, and whatever the heck you call the iPod OS. I use a wide variety of tools on each platform – some redundant, some unique. And I'm continually tweaking the interaction and integration between these devices and their respective operating systems and application sets to achieve an integrated, accessible from anywhere workspace. This is increasingly made possible through the use of web services as I have had more bad experiences with syncing tools than any other kind of software and the number of devices and platforms I currently use, combined with my frequent change in lat-long coordinates makes local, cable-based syncing impractical.

From an application perspective, I've been a big fan and outspoken advocate for Microsoft Outlook for a long time (no big surprise to regular readers) and have developed training courses in its use and recently completed The Unofficial Guide to Microsoft Outlook 2007 for Wiley which will be available around the end of this month. I also am a big fan of Mindjet MindManager, an application that I use every day on both my Tablet PC and my MacBook. But increasingly, I'm migrating to web-based tools for more and more of the core work I do. Gmail and Google Calendar are both critical tools in my productivity system, as are del.icio.us, Flickr, and DropSend. The Foxmarks extension keeps my Firefox bookmarks synced between the Mac and Tablet PC while, as I documented in a recent post, Spanning Sync on the iCal side of the equation and SyncMyCal on the Outlook side use Google Calendar as the glue to keep my calendar up-to-date and accessible from any device and location.

So, I won't be a spoiler and tell you Ed's picks for best and worst Windows ever. But I will tell you that – hands down, no argument allowed – the worst version of Windows ever was the Migraine Edition, otherwise known as Windows Me. Aside from the introduction of System Restore, I have not one good thing to say about this inexcusable release.

Best? That's a bit harder. On the one hand, there is no denying that Windows 2000 was a fantastic, stable, new-era kind of release – one that continues to be used my many people and organizations I know to this day. But I think I'm going to have to go with XP Service Pack 2 which I believe was actually worthy of being called a new version. FWIW, Jim Allchin told Mary Jo Foley the same thing in a recent interview. Not only did SP2 make XP a much better-behaved OS, it introduced the Tablet PC 2005 Edition which elevated the Tablet PC from a parlor trick to a truly productive mobile computing platform.

Windows Vista? Too early to say in my opinion. I've now used Vista on three PCs with good results on two. The jury is still out on the third. On the Dell Latitude D620, Vista Ultimate ran smooth as silk with full Aero eye candy and excellent overall performance. On the Lenovo X60t, Vista Business runs just as well (although Aero is a bit of a resource hog on the Intel graphics chipset, it only becomes an issue when I have a large number of applications running) and shows off the tremendous improvements in ink and speech recognition the new version of Windows provides.

On the Asus R2H UMPC, Vista is still a work in progress. Some essential drivers are still unavailable and until that dust settles, it will be hard to declare victory (I keep Vista on the device) or defeat (I go back to Windows XP SP2). I just got the Asus two days ago and am waiting on a bigger RAM module and time to install a few recently released and forthcoming drivers before I will be in a position to render a qualified opinion. I'll be posting more about the UMPC experience and this particular unit in the coming days and weeks. I'm also hoping to get my hands on another popular UMPC model so I can better gauge the usefulness and desirability of that form factor.

What's your opinion? Is there a version of Windows you found particularly great or horrible? I think it's important to make that evaluation in the context of the times in which each release was made. There's no fair way to compare versions head-to-head.