Windows 98 can still be a good choice

Software upgrade costs
Software upgrade cost probably is the first thing that comes to mind as a reason to stick with Windows 98 rather than upgrade. Bill Gates is no Linus Torvalds, so naturally you're going to have to pay to upgrade Windows 98.

Upgrade costs will vary. If you don't have a licensing agreement with Microsoft such as OpenLicense, you'll have to upgrade workstations one at a time. A quick look at CNET Shopper.com will show that you'll spend about $175 per machine to upgrade to Windows XP Professional from Windows 98. At a time when IT budgets are increasingly getting squeezed, you can probably use that money for other things in your organisation.

Hardware upgrade costs
Beyond the mere cost of the software, leaving Windows 98 behind will probably force you to make some hefty hardware investments. Microsoft's minimum requirements for Windows XP Professional are a 233MHz Pentium II PC with 64MB of RAM and 1.5GB of free hard drive space. As you probably know, even though XP will boot under such a configuration, it won't be very useful. You need at least a 450MHz processor with 256MB of RAM to get much work done. Although such a practical minimum seems puny compared to what's inside today's newest machines, chances are most of your existing workstations are closer to XP's practical minimum.

At the same time, consider the Windows 98 minimum recommendations: a 486 processor with 24MB of RAM and 400MB of free hard drive space. Therefore, a workstation that will barely boot Windows XP Professional will run Windows 98 nicely. Even at XP's practical minimum, Windows 98 will scream.

Prices for hardware upgrades such as hard drives and RAM may be falling, but as with software upgrade costs, every little bit adds up. Factor in the time it takes to install the hardware upgrades and the number of workstations in your organisation, and you're talking real money after a while -- for not much of a performance improvement over your existing hardware and Windows 98.

Application compatibility
Microsoft included the Application Compatibility Wizard in both Windows 2000 Professional and Windows XP to help older applications run on them. Many times, however, older applications -- especially custom ones written for a DOS environment -- just won't run in Windows 2000 or XP.

Even some Windows programs present problems. Often an application's Setup Wizard will check to see what version of Windows you're running before installing. If it's an older application, it may not understand what Windows 2000 or Windows XP is, and fail to install because it says you have the "wrong" version. If the Application Compatibility Wizard can't fix the Setup Wizard and if you can't get a newer version of the program, then you're stuck.

Many newer applications won't run on older operating systems like Windows 95. Window 98, especially SE, doesn't have as much problem with non-support from newer applications as does Windows 95. Even though finding newer applications that will run under Windows 98 may be more of a problem in the future, consider the fact that if your users want to use a newer, more powerful application that won't run under Windows 98, they'll probably also need a new machine with more hardware power anyway -- complete with a new "free" copy of Windows XP.

Hardware compatibility
As Greg pointed out in his article about why you should abandon Windows 98, Microsoft no longer requires that hardware manufacturers create Windows 98 drivers. In the future, this may logically cause them not to create Windows 98 drivers to save development costs. Oftentimes, however, due to Windows 98's huge installed base, manufacturers will indeed create new 98 drivers to support that base.

Your biggest hardware compatibility problem probably won't come with new hardware supporting Windows 98. When upgrading, your problem will come from getting the new OS to work with your existing hardware.

Windows XP does a better job of supporting hardware than did Windows NT Workstation, from which it was derived, but there still aren't as many drivers available for it as there are for Windows 98. I detailed how to get some non-XP drivers to work on XP in the article "Newer isn't always better when it comes to Windows XP drivers" (free registration required), but if an NT or 2000 driver won't work for a particular device, then your only practical solution is to get rid of it and buy a replacement.

Training issues
Because Windows 98 has been around for over five years, your users probably know their way around it and are comfortable with it. They (should) know by now where most of the common menu choices are, and maybe even how to do some self-troubleshooting when problems arise.

Be mindful of the training issues you'll face when you put XP's Luna interface on a non-technical user's desk and they see it for the first time after using Windows 98 for five years. Even if you enable the Classic interface, the layout is different enough from Windows 98 that you'll need to spend time showing them where to find common things like printers and programs.

General support issues
Not only are users comfortable with Windows 98, chances are so are you. As you know by now, if you look at Windows 98 cross-eyed, it will blue-screen on you. Admittedly, Windows XP is more stable overall than Windows 98. Having supported 98 for so long, you're also probably familiar with all of the tricks necessary to keep the OS working on a workstation. You know the tweaks to make, the hardware and software combinations to use and not to use, and probably have a decent investment in Windows 98 third-party support utilities.

By placing an upgraded OS on a workstation, you're adding a whole new layer of complexity. Not only do you have to overcome the general quirks of the new OS, but you also have to know how the OS behaves on a particular piece of hardware. Sometimes it's just easier -- which translates to cheaper and more efficient -- to keep supporting something that works rather than tossing something new and more complex on top of it. By upgrading a machine, not only do you have to make fresh investments of time and energy in performing the upgrade and responding to the new support calls for it, but you're also abandoning the efficiencies in answering questions about the OS you've supported for so long.

If it ain't broke, don't fix it
It's not often you hear the words "ain't broke" used in conjunction with an OS as fragile as Windows 98. Sure, it's not as new as, as robust as, and sometimes not as stable as Windows 2000 or XP. Compared side-by-side with these newer operating systems, as well as Linux, Windows 98 is nowhere in the same class. Windows 98's time has definitely come to be thrown on the pile.

However, things always aren't so cut-and-dried in a business environment. Ask yourself three quick questions:

Are my users are still productive on this Windows 98 system?
Do all of my applications run on Windows 98?
Will I be keeping the hardware the user is using for a while longer?

Chances are, if you've answered yes to all three questions, you're better off not upgrading Windows 98. Rather, wait until you purchase new hardware and applications for the user and introduce the new OS at the same time.