Programmers are in a race with the Universe to create bigger and better idiot-proof programs, while the Universe is trying to create bigger and better idiots. So far the Universe is winning.
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WinDirStat - Graphical representation of what's eating your disk:
http://windirstat.info/
screen + irssi -- OK, not Windows apps, but I use them from Windows ssh as much as from Linux.
Awesome blog, BTW.
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