make sure you are using Isapi rewrite 3 and not 2 as only 3 works with apache rules make sure wordpress is giving you the Apache rules and not the IIS rules. If it is causing you that much grief, it probably will just be easier to give Apache a try. However I would recommend upgrading to windows 2008/IIS7 as it is better in many ways, it is however significantly different and does have a fair old learning curve.
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