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Let's talk more about softwares....how about these relatively new 'FREE' softwares from Microsoft......(ok, some are not that new).

MS Port Reporter [Network Port Monitoring]
MS AntiSpyware (beta) [spyware/adware]
MS Log Parser [especially for IIS logs]
Malicious Software Removal Tool [Malware]
Windows XP Video Decoder Checkup Utility [video codec]
Microsoft Best Practices Analyzer for MS SQL server 2000 and Exchange server [For SQL/Exchange server Admins]
Tweakomatic ['nuf said]
Update for Windows XP Service Pack 2 (KB884020) [update]
Codec Installation Package [video codecs update]
Microsoft ActiveSync 3.8 [update]

I haven't personally tried some of these softwares (I use other third party apps) , But I believe it's a must have for regular to intermediate users.

[Tidbits]
Did you know that Windows 2003 servers automatically logs IP Addresses of ALL 'failed' authentication requests? (that login pop-ups, even for web access).