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really, honestly and sincerely do not mean to be even the slightest bit rude with this comment, but that phrase really shows how out of touch you are with modern web development. I'm sorry, but you're wholly incorrect.
People who love their old browsers will continue to hold onto them. There are still people using ancient version of Netscape, Lynx and Mosaic for that matter. The choice is theirs, naturally. But the progression of the web and what is available in terms of functionality, and how the specs and technology has grown since those old browsers were maintstrea has far surpassed their capabilities. Additionally, supporting platforms that the platform manufacturer doesnt even support any longer makes no business sense. As a courtesy you support these aging techs just long enough for the stragglers to catch up.
OpusCroakus, to address your Windows 2000 Server question, the answer is simple; install Firefox. It works just as well in a server environment. In fact, we have a trend going here where that is one of the first things installed on our servers. There's really no argument at that point for not using a modern browser. Both Mozilla and Opera teams have shown that you can certainly provide a build that runs well on machines not running Windows XP.
Those resisting updating seriously need to ask yourselves why. Personally I wait at least a year before updating my Operating System to the next big one. And I get that, because I like to wait for all the bugs to be ironed out. That's a valid argument. But, as an example, hanging on to say Windows 98 for 10 years, just for the sake of argument or because 'i want to' and then expecting all new software coming out to support it is just plain silly. 1997 has come and gone my friends. IE6 is a dying beast.