With the arrival of Windows 7, a lot of people are at least thinking about upgrading Windows. Alas, I have some bad news for you. Upgrading to Windows 7 from XP is very difficult, and Vista is proving troublesome as well.
That is, if you can upgrade at all. Many XP users with older PCs simply won't have the CPU horsepower or sufficient RAM to run Windows 7 well. To see if your PC can manage it, download and run Microsoft's Windows 7 Upgrade Advisor. Microsoft says you need at least a 1 GHz processor and 1 GB of RAM for Windows 7. I think it's safer to double both those requirements before it will be worth your time to move from XP to Windows 7.
If you do have sufficiently powerful hardware, you need to be ready to re-install all your applications and data. There's no built-in way to do an in-place upgrade from XP to 7. I haven't tested it yet, but LapLink's PCmover Windows 7 Upgrade Assistant claims to be able to make an in-place upgrade possible. Before trying it, though, I'd, as Sharon Machlis suggests, back up everything in sight and make sure I have my software installation programs at hand. It's not that I don't trust LapLink, but with any upgrade like this there are so many things that could go wrong, I want to be darn sure I'm not going to lose anything valuable.
My recommendation? An XP user's best way to 'upgrade' will be to buy a new Windows 7 PC.
The theory was that upgrading from Vista to Windows 7 would be much easier than from XP. I've found it so, but I also haven't seen enough of a difference between Windows 7 and Vista that a happy Vista user would want to upgrade. If, like so many others, you really didn't like Vista at all, I strongly recommend making the upgrade.
Just be aware though that you can't upgrade from 32-bit version of Vista to a 64-bit edition of Windows 7. A lot of people found out the hard way that you can't get there from here.
Microsoft has responded by making an ISO image of Windows 7 available for those who have had trouble with the previous update program. Even with this more reliable way of upgrading, you should keep in mind that, just like XP users, when you move from 32-bit Vista to 64-bit Windows, you'll need to re-install your applications and restore your data.
Even if you can move straight from one version of Windows to another with an in-place update, the process is going to take you a long time. How long? Microsoft warned people that it could take up to 20-hours. And now we know they weren't kidding. I've heard from numerous people that their upgrade had eaten up their entire day, and they still weren't done yet. No matter what kind of Windows 7 upgrade you plan on doing, you should plan to spending a weekend on it. I've done it faster and with less trouble, but then I install operating systems almost every other day.
Last, but not least: when it comes to device support, while Windows 7 isn't nearly as bad as Vista first was, Windows 7 does not have device support for a lot of relatively common equipment. No what version of Windows you use, for most people the easiest way to 'upgrade' is just going to be to bite the bullet and buy a new PC.
Mac users have it much easier. To move from Leopard to Snow Leopard, you just put the Snow Leopard DVD in the drive, let it run, and that's it you're done.
That's one of the blessings of a Mac. Yes, they are more expensive than PCs, but upgrading them is as simple as simple can be. It takes me an average of four hours to upgrade a Vista system to Windows 7, and eight hours from XP to Windows 7. It takes me less than an hour with Snow Leopard. 'Nuff said.
Ubuntu is almost as easy. With Ubuntu, you need to burn the ISO image to a DVD or USB stick. After that, just like the Mac, you just stick the media in, and, in just short of an hour, you're ready to go with the latest version of Ubuntu.
The same is true of any Linux distribution. Even switching from one version of Linux to another, say Fedora to openSUSE, is easier and far less time-consuming that any of the Windows 7 upgrades.
Of course, there's no fast and easy way to move from any version of Windows to a Mac or Linux. That said, once you make the move from Windows to an alternative you won't have to worry with future tedious updates. Is that reason enough to switch? Probably not, but it is to something to think about somewhere around hour five of your Windows upgrade.