I've just read the Most useful AutoHotKey scripts question and that got me thinking about automation and repetitive tasks.
Which automated task, once you got it in place and functioning, really made a difference in how you go about your day?
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robocopy /E /DCOPY:T /MT:2 \\live.sysinternals.com\tools C:\Path\To\SysinternalsSuite /XF Thumbs.db)
Website macros! I work with many websites (Email, salesfore, SAP web client, intranet, blogs, Stackoverflow etc) each day and automated all routine logins and navigation with iMacros (free Firefox addon).