I heard about Launchy (OSS, http://www.launchy.net/) from Lifehacker, and it's pretty fun. I've been meaning to stick a copy of the API + .js in a launchy directory... Also, I'm not up on my Windows coding, but it also supports plugins (DLL's)...could possibly integrate with jQueryHelp?
I just realized Launchy has a portable mode (USB), hrmmm
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