Linked by Robert Gering on Tue 17th Sep 2002 18:11 UTC
First, a little background. I am a Windows user who has been using Windows since 3.1. I am not a programmer or a developer, I am a user. I process photos, use the internet, e-mail, write letters, play the ever important games and even use it to develop my comic strips. I am not computer illiterate and I use my computer with confidence and skill. Now with that said. I hate Windows.
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I'm not sure if there is a good answer for you if you are scared away by product updates. Although I'm a techno weenie and can deal with patching, etc. I know that most people are not and just want something that works. I think XP works well but still isn't there for the common Joe. I don't think anything is there yet. Every platform has its faults. Computers are still computers and require a decent amount of maintenance, especially in this Internet age.
One thing to consider in your search is to look at VMWare... you can run multiple virtual PCs within your own. You can use it to test the waters with Linux or whatever, and also use it to run the legacy apps you mentioned on a box with a newer OS like XP.
You have tried XP, right?